Abstract
A review with 141 references on [4+2] cycloaddition reactions involving the indole nucleus.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsNotes
- 1.
For additional examples, see [127].
References
Juhl M, Tanner D (2009) Recent applications of intramolecular Diels–Alder reactions to natural product synthesis. Chem Soc Rev 38:2983–2992
Tadano K-i (2009) Natural product synthesis featuring intramolecular Diels–Alder approaches – Total Syntheses of tubelactomicins and spiculoic acid A. Eur J Org Chem 4381–4394
Hassfeld J, Kalesse M et al (2005) Asymmetric total synthesis of complex marine natural products. Adv Biochem Eng Biotechnol 97:133–203
Takao K, Munakata R et al (2005) Recent advances in natural product synthesis by using intramolecular Diels–Alder reactions. Chem Rev (Washington, DC) 105:4779–4807
Tietze LF, Rackelmann N (2004) Domino reactions in the synthesis of heterocyclic natural products and analogs. Pure Appl Chem 76:1967–1983
Suzuki Y, Murata T et al (2002) The intramolecular Diels–Alder strategy: applications to total synthesis of natural products. Yuki Gosei Kagaku Kyokaishi 60:679–690
Nicolaou KC, Snyder SA et al (2002) The Diels–Alder reaction in total synthesis. Angew Chem Int Ed 41:1668–1698
Helmchen G, Goeke A et al (1991) Cyclopentanoid natural products via asymmetric Diels–Alder reactions. Stud Nat Prod Chem 8:139–158
Lee L, Snyder JK (1999) Indole as a dienophile in inverse electron demand Diels–Alder and related reactions. Adv Cycloaddit 6:119–171
Boger DL (1996) Azadiene Diels–Alder reactions: scope and applications. Total synthesis of natural and ent-fredericamycin A. J Heterocycl Chem 33:1519–1531
Boger DL, Patel M (1989) Recent applications of the inverse electron demand Diels–Alder reaction. Prog Heterocycl Chem 1:30–64
Boger DL, Panek JS et al (1992) Preparation and Diels–Alder reaction of a reactive, electron-deficient heterocyclic azadiene: dimethyl 1, 2, 4, 5-tetrazine-3, 6-dicarboxylate. 1, 2-Diazine (dimethyl 4-phenyl-1, 2-diazine-3, 6-dicarboxylate) and pyrrole (dimethyl 3-phenylpyrrole-2, 5-dicarboxylate) introduction. Organic Synth 70:335
Gonzalez JC, Lobo-Antunes J et al (2002) Synthesis of angular pyrrolocoumarins. Synthesis 475–478
Helliwell M, Corden S et al (2007) 5, 7-Diacetyl-13-benzyl-7, 8-dihydro-5H, 8aH, 13H-diindolo[2, 3-c;2, 3-d]pyrimidin-8-yl acetate, the result of an intramolecular cycloaddition between an N-benzylindole and a 1, 2, 4, 5-tetrazine. Acta Crystallogr Sect E Struct Rep Online E63:o1993–o1995
Giomi D, Cecchi M (2002) Study on direct benzoannelations of pyrrole and indole systems by domino reactions with 4, 5-dicyanopyridazine. Tetrahedron 58:8067–8071
Haider N, Kaeferboeck J (2004) Intramolecular [4 + 2]-cycloaddition reactions of indolylalkylpyridazines: Synthesis of annulated carbazoles. Tetrahedron 60:6495–6507
Kobayashi S (2002) Catalytic enantioselective aza Diels–Alder reactions. Cycloaddit React Org Synth 187–209
Sarkar N, Banerjee A et al (2008) [4 + 2] Cycloadditions of N-alkenyl iminium ions: Structurally complex heterocycles from a three-component Diels–Alder reaction sequence. J Am Chem Soc 130:9222–9223
Noland WE, Kedrowski BL (1999) Synthesis of angular quinoid heterocycles from 2-(2-nitrovinyl)-1, 4-benzoquinone. J Org Chem 64:596–603
Blattes E, Fleury M-B et al (2004) Simultaneously electrogenerated cycloaddition partners for regiospecific inverse-electron-demand Diels–Alder reactions: a route for polyfunctionalized 1, 4-benzoxazine derivatives. J Org Chem 69:882–890
Hu Z-L, Qian W-J et al (2009) Transformation of reactive isochromenylium intermediates to stable salts and their cascade reactions with olefins. Org Lett 11:4676–4679
May JA, Zeidan RK et al (2003) Biomimetic approach to communesin B (a.k.a. nomofungin). Tetrahedron Lett 44:1203–1205
Steinhagen H, Corey EJ (1999) A convenient and versatile route to hydroquinolines by inter- and intramolecular aza-Diels–Alder pathways. Angew Chem Int Ed 38:1928–1931
Crawley SL, Funk RL (2003) A synthetic approach to nomofungin/communesin B. Org Lett 5:3169–3171
Crawley SL, Funk RL (2006) Generation of aza-ortho-xylylenes via ring opening of 2-(2-acylaminophenyl)aziridines: application in the construction of the communesin ring system. Org Lett 8:3995–3998
George JH, Adlington RM (2008) A synthetic approach to the communesins. Synlett 2093–2096
Fuchs JR, Funk RL (2004) Total synthesis of (+-)-perophoramidine. J Am Chem Soc 126:5068–5069
Menozzi C, Dalko PI et al (2006) Concise synthesis of the (+/−)-Nb-desmethyl-meso-chimonanthine. Chem Commun (Cambridge, U K). 4638–4640
Biolatto B, Kneeteman M et al (1999) Diels–Alder reactions of N-tosyl-3-nitroindole and dienamides: synthesis of intermediates of Aspidospermine alkaloids. Tetrahedron Lett 40:3343–3346
Biolatto B, Kneeteman M et al (2000) N, N-diethyl-1-tosyl-3-indoleglyoxamide as a dienophile in Diels–Alder reactions. Hyperbaric vs. thermal conditions. Molecules 5:393–395
Kishbaugh TLS, Gribble GW (2001) Diels–Alder reactions of 2- and 3-nitroindoles. A simple hydroxycarbazole synthesis. Tetrahedron Lett 42:4783–4785
Chataigner I, Panel C et al (2007) Sulfonyl vs. carbonyl group: which is the more electron-withdrawing? Chem Commun (Cambridge, UK) 3288–3290
Chataigner I, Hess E et al (2001) Activation of the dienophilicity of indoles in normal electron demand [4 + 2] cycloadditions under high pressure. Org Lett 3:515–518
Chretien A, Chataigner I et al (2003) Complete and remarkable reversal of chemoselectivity in [4 + 2] cycloadditions involving electron-poor indoles as dienophiles. Diels–Alder versus hetero-Diels–Alder processes. J Org Chem 68:7990–8002
Victoria Gomez M, Aranda AI et al (2009) Microwave-assisted reactions of nitroheterocycles with dienes. Diels–Alder and tandem hetero Diels–Alder/[3, 3] sigmatropic shift. Tetrahedron 65:5328–5336
Lynch SM, Bur SK et al (2002) Intramolecular amidofuran cycloadditions across an indole p-Bond: an efficient approach to the aspidosperma and strychnos ABCE core. Org Lett 4:4643–4645
Zhang H, Boonsombat J et al (2007) Total synthesis of (+-)-strychnine via a [4 + 2]-cycloaddition/rearrangement cascade. Org Lett 9:279–282
Boonsombat J, Zhang H et al (2008) A general synthetic entry to the pentacyclic strychnos alkaloid family, using a [4 + 2]-cycloaddition/rearrangement cascade sequence. J Org Chem 73:3539–3550
Steinhardt SE, Vanderwal CD (2009) Complex polycyclic lactams from pericyclic cascade reactions of Zincke aldehydes. J Am Chem Soc 131:7546–7547
Steinhardt SE, Silverston JS et al (2008) Stereocontrolled synthesis of Z-dienes via an unexpected pericyclic cascade rearrangement of 5-amino-2, 4-pentadienals. J Am Chem Soc 130:7560–7561
Sissouma D, Maingot L et al (2006) Concise and efficient synthesis of calothrixin B. J Org Chem 71:8384–8389
Poumaroux A, Bouaziz Z et al (1997) Regiospecific hetero Diels–Alder synthesis of pyrido[2, 3-b]- and pyrido[3, 2-b]carbazole-5, 11-diones. Heterocycles 45:585–596
Poumaroux A, Bouaziz Z et al (1999) Regiospecific synthesis of pyrido[3, 4-b]- and pyrido[4, 3-b]carbazole-5, 11-dione derivatives. Evaluation of their in vitro antifungal or antiprotozoological activities. Chem Pharm Bull 47:643–646
Carr G, Chung MKW et al (2008) Synthesis of indoleamine 2, 3-dioxygenase inhibitory analogues of the sponge alkaloid exiguamine A. J Med Chem 51:2634–2637
Tapia RA, Prieto Y et al (2003) Synthesis and antiprotozoal evaluation of benzothiazolopyrroloquinoxalinones, analogues of kuanoniamine A. Bioorg Med Chem 11:3407–3412
Tapia RA, Prieto Y et al (2002) Synthesis and antileishmanial activity of indoloquinones containing a fused benzothiazole ring. Eur J Org Chem 4005–4010
Bouaziz Z, Gherardi A et al (2002) Synthesis of carbazolequinone derivatives as inhibitors of Toxoplasma gondii purine nucleoside phosphorylase. Eur J Org Chem 1834–1838
Beneteau V, Besson T (2001) Synthesis of novel pentacyclic pyrrolothiazolobenzoquinolinones, analogs of natural marine alkaloids. Tetrahedron Lett 42:2673–2676
Weeratunga G, Prasad GKB et al (1990) Regioselective Diels–Alder reactions of N-cyanoindole-4, 7-diones: elaboration of the A-ring of the kinamycins on a BC ring template. Tetrahedron Lett 31:5713–5716
Andersen R, Leblanc M et al (2008) Syntheses of substituted tryptophan quinones as inhibitors of indoleamine 2,3-dioxygenase (IDO). WO2008052352
Chernov SV, Shults EE et al (2000) Synthetic transformations of higher terpenoids. V. 2-Methyl-4, 5-dioxo-3-ethoxycarbonyl-4, 5-dihydroindole, a new dienophile. Synthesis of indoloterpenes from levopimaric acid. Russ J Org Chem 36:1623–1633
Cai P, Snyder JK (1990) Preparation, reactivity, and neurotoxicity of tryptamine-4, 5-dione. Tetrahedron Lett 31:969–972
Buszek KR, Luo D et al (2007) Indole-derived arynes and their Diels–Alder reactivity with furans. Org Lett 9:4135–4137
Brown N, Luo D et al (2009) Regioselective Diels–Alder cycloadditions and other reactions of 4, 5-, 5, 6-, and 6, 7-indole arynes. Tetrahedron Lett 50:63–65
Buszek KR, Brown N et al (2009) Concise total synthesis of (+-)-cis-trikentrin A and (+-)-herbindole A via intermolecular indole aryne cycloaddition. Org Lett 11:201–204
Brown N, Luo D et al (2009) New synthesis of (+-)-cis-trikentrin A via tandem indole aryne cycloaddition/Negishi reaction. Applications to library development. Tetrahedron Lett 50:7113–7115
Bronner SM, Bahnck KB et al (2009) Indolynes as electrophilic indole surrogates: fundamental reactivity and synthetic applications. Org Lett 11:1007–1010
Pindur U (1988) New Diels–Alder reactions with vinylindoles. A regio- and stereocontrolled access to annellated indoles and derivatives. Heterocycles 27:1253–1268
Pindur U (1995) Cycloaddition reactions of indole derivatives. Adv Nitrogen Heterocycl 1:121–172
Eitel M, Pindur U (1990) Reactions of 2-vinylindoles with carbodienophiles: synthetic and mechanistic aspects. J Org Chem 55:5368–5374
Abbiati G, Canevari V et al (2007) Diels–Alder reactions of 2-vinylindoles with open-chain C=C dienophiles. Eur J Org Chem 517–525
Back TG, Bethell RJ et al (2001) Preparation of vinylogous 2-sulfonylindolines by the palladium-catalyzed heteroannulation of o-iodoanilines with dienyl sulfones and their further transformation to indoles and carbazoles. J Org Chem 66:8599–8605
Back TG, Pandyra A et al (2003) Regiochemical switching in Diels–Alder cycloadditions by change in oxidation state of removable diene sulfur substituents. Synthesis of carbazoles by sequential heteroannulation and Diels–Alder cycloaddition. J Org Chem 68:3299–3302
Wilkens J, Kuehling A et al (1987) Hetero-cope rearrangements. VI. short and stereoselective synthesis of 2-vinylindoles by a tandem-process. Tetrahedron 43:3237–3246
Blechert S, Knier R et al (1995) Domino reactions – new concepts in the synthesis of indole alkaloids and other polycyclic indole derivatives. Synthesis 592–604
Cavdar H, Saracoglu N (2006) Synthesis of new 2-vinylation products of indole via a Michael-type addition reaction with dimethyl acetylenedicarboxylate and their Diels–Alder reactivity as precursors of new carbazoles. J Org Chem 71:7793–7799
McCort G, Duclos O et al (1999) A versatile new synthesis of 4-aryl- and heteroaryl-[3, 4-c]pyrrolocarbazoles by [4+2] cycloaddition followed by palladium catalyzed cross coupling. Tetrahedron Lett 40:6211–6215
Marques MMB, Lobo AM et al (1999) A Diels–Alder, retro-Diels–Alder approach to arcyriaflavin-A. Tetrahedron Lett 40:3795–3796
Barry JF, Wallace TW et al (1995) On the [4 + 2] cycloaddition approach to indolo[2, 3-a]carbazoles. Tetrahedron 51:12797–12806
Kuethe JT, Davies IW (2004) Formal [4+2] cycloaddition reactions of N-sulfonyl-2, 2'-biindoles: synthesis of indolo[2, 3-a]carbazoles and indigo azines. Tetrahedron Lett 45:4009–4012
Kuehne ME, Roland DM et al (1978) Studies in biomimetic alkaloid syntheses. 2. Synthesis of vincadifformine from tetrahydro-b-carboline through a secodine intermediate. J Org Chem 43:3705–3710
Overman LE, Sworin M (1985) Recent advances in the total synthesis of pentacyclic Aspidosperma alkaloids. Alkaloids: Chem Biol Perspect 3:275–307
Kalaus G, Vago I et al (1995) Synthesis of vinca alkaloids and related compounds. 776. Synthesis and ring transformations of compounds with the aspidospermane- and D-noraspidospermane skeleton. A formal synthesis of (+-)-12-demethoxy-N(1)-acetylcylindrocarine. Nat Prod Lett 7:197–204
Pegram JJ, Anderson CB (1988) Synthesis of 1-benzyldimethylsilyl-4-phenylthio-1, 3-butadiene. New diene-regenerable Diels–Alder synthon. Tetrahedron Lett 29:6719–6720
Kalaus G, Juhasz I et al (1997) Synthesis of vinca alkaloids and related compounds. 90. New results in the synthesis of alkaloids with the aspidospermane skeleton. First total synthesis of (+-)-3-oxominovincine. J Org Chem 62:9188–9191
Kalaus G, Leder L et al (2003) Synthesis of vinca alkaloids and related compounds. Part 102. Simple synthesis and ring transformation of (+-)-minovincine. First synthesis of (+-)-vincaminine. Tetrahedron 59:5661–5666
Eles J, Kalaus G et al (2002) Synthesis of vinca alkaloids and related compounds. Part 101: A new convergent synthetic pathway to build up the aspidospermane skeleton. Simple synthesis of 3-oxovincadifformine and 3-oxominovincine. Attempts to produce 15b-hydroxyvincadifformine. Tetrahedron 58:8921–8927
Kalaus G, Toth F et al (2006) Synthesis of vinca alkaloids and related compounds. Part 103. Recognition of an unexpected reaction and its application in building the aspidospermane skeleton. Simple synthesis of 15b-hydroxyvincadifformine. Heterocycles 68:257–270
Kalaus G, Juhasz I et al (2000) Synthesis of vinca alkaloids and related compounds. Part 94. Epimerization of compounds with aspidospermane and D-secoaspidospermane skeleton. J Heterocycl Chem 37:245–251
Toth F, Kalaus G et al (2006) Synthesis of vinca alkaloids and related compounds. Part 105: Efficient convergent synthetic pathway to the ibophyllidine skeleton and synthesis of (+-)-19-hydroxy-ibophyllidine and (+-)-19-hydroxy-20-epiibophyllidine. Tetrahedron 62:12011–12016
Toth F, Kalaus G et al (2006) Synthesis of vinca alkaloids and related compounds. Part 106. An efficient convergent synthetic pathway to build up the ibophyllidine skeleton II. Total synthesis of (+-)-deethylibophyllidine and (+-)-14-epi-deethylibophyllidine. Heterocycles 68:2301–2317
Toth F, Kalaus G et al (2007) Synthesis of vinca alkaloids and related compounds. Part 107. An efficient convergent synthetic pathway to build up the ibophyllidine skeleton. III. Total synthesis of (+-)-ibophyllidine and (+-)-20-epiibophyllidine. Heterocycles 71:865–880
Toth F, Kalaus G et al (2007) Synthesis of vinca alkaloids and related compounds. Part 108: Efficient convergent synthetic pathway to the ibophyllidine skeleton IV. First synthesis of (+-)-18-hydroxy-20-epiibophyllidine. Tetrahedron 63:7823–7827
Toth F, Kalaus G et al (2008) Synthesis of vinca alkaloids and related compounds. Part 109. An intramolecular [4+2] cycloaddition mediated biomimetic synthesis of (+-)-iboxyphylline. Heterocycles 75:65–76
Toth F, Olah J et al (2008) Synthesis of Vinca alkaloids and related compounds. Part 110: A new synthetic method for the preparation of pandoline-type alkaloid-like molecules. Tetrahedron 64:7949–7955
Vago I, Kalaus G et al (2001) Synthesis of vinca alkaloids and related compounds. 95. Attempted build-up of the aspidospermidine skeleton by [4+2] cycloaddition. Some unexpected reactions, and formation of a new ring system. Heterocycles 55:873–880
Fayol A, Fang Y-Q et al (2006) Synthesis of 2-vinylic indoles and derivatives via a Pd-catalyzed tandem coupling reaction. Org Lett 8:4203–4206
Passarella D, Giardini A et al (2001) Cyclodimerization of indol-2-ylacetylenes. An example of intermolecular enyne-alkyne cycloaddition. J Chem Soc, Perkin Trans 1 127–129
Ishikura M, Uchiyama H et al (2001) Cycloaddition reaction of 2-allenylindoles with diethyl acetylenedicarboxylate under thermal and high pressure conditions. J Heterocycl Chem 38:675–678
Anisimova NA, Berkova GA et al (2006) Reaction of methyl 3-nitroacrylate with 3-(2-nitroethenyl)indole. Russ J Org Chem 42:1246–1247
Wolter M, Borm C et al (2001) Enantiopure polycycles by sequential cycloadditions. Eur J Org Chem 4051–4060
Merour J-Y, Bourlot A-S et al (1995) [4+2] versus [2+2] cycloadditions with 1-ethoxyethene and heterocyclic aldehydes; formation of vinyl compounds. Tetrahedron Lett 36:3527–3530
Le Strat F, Maddaluno J (2002) New carbanionic access to 3-vinylindoles and 3-vinylbenzofurans. Org Lett 4:2791–2793
Le Strat F, Vallette H et al (2005) Access to tri- and tetracyclic structures by thermally promoted and high-pressure-promoted [4 + 2] cycloadditions of 2-, 3- or 4-vinyl-substituted binuclear heterocycles. Eur J Org Chem 5296–5305
Pindur U, Gonzalez E et al (1997) [4+2]Cycloaddition of indole derivatives with bismaleimides: a route to new biscarbazoles. J Chem Soc, Perkin Trans 1 1861–1867
Lopez-Alvarado P, Alonso MA et al (2001) One-pot assembly of large heterocyclic quinones through three-component reactions. Tetrahedron Lett 42:7971–7974
Gharagozloo P, Miyauchi M et al (1998) Intramolecular Diels–Alder reactions of 3-(tetrahydropyridinyl)indoles: stereoselective synthesis of novel pentacyclic ring systems. J Org Chem 63:1974–1980
Desarbre E, Bergman J (1998) Synthesis of symmetric and non-symmetric indolo[2,3-c]carbazole derivatives: preparation of indolo[2,3-c]pyrrolo[3,4-a]carbazoles. J Chem Soc, Perkin Trans 1 2009–2016
Somei M, Kodama A (1992) A novel synthesis of 2, 2'-bisindole and its application for the synthesis of indolo[2, 3-a]carbazole derivatives. Heterocycles 34:1285–1288
Bleile M, Wagner T et al (2005) Synthesis of substituted pyrrolo[3, 4-a]carbazoles. Helv Chim Acta 88:2879–2891
Bleile M, Otto H-H (2005) Substituted pyrrolo[3, 4-a]carbazoles from reactions between 3-(1-methoxy-vinyl)indoles and maleimides. Monatsh Chem 136:1799–1809
Hugon B, Pfeiffer B et al (2003) Synthesis of granulatimide analogues bearing a maleimide instead of an imidazole heterocycle. Tetrahedron Lett 44:3935–3937
Henon H, Anizon F et al (2006) Synthesis of dipyrrolo[3, 4-a:3, 4-c]carbazole-1, 3, 4, 6-tetraones bearing a sugar moiety. Tetrahedron 62:1116–1123
Joseph B, Facompre M et al (2001) Synthesis, cytotoxicity, DNA interaction and topoisomerase II inhibition properties of tetrahydropyrrolo[3, 4-a]carbazole-1, 3-dione and tetrahydropyrido-[3, 2-b]pyrrolo[3, 4-g]indole-1, 3-dione derivatives. Bioorg Med Chem 9:1533–1541
Markgraf JH, Synder SA et al (1998) A concise route to isocanthin-6-one. Tetrahedron Lett 39:1111–1112
Snyder SA, Vosburg DA et al (2000) Intramolecular hetero Diels–Alder routes to g-carboline alkaloids. Tetrahedron 56:5329–5335
Markgraf JH, Finkelstein M et al (1996) Canthine analogs via intramolecular Diels–Alder reactions. Tetrahedron 52:461–470
Grieco PA, Kaufman MD (1999) Intramolecular imino Diels–Alder reaction of a 3-vinyl indole: application to a total synthesis of (+-)-eburnamonine. J Org Chem 64:7586–7593
Rosillo M, Dominguez G et al (2004) Tandem enyne metathesis-Diels–Alder reaction for construction of natural product frameworks. J Org Chem 69:2084–2093
Chataigner I, Piettre SR (2007) Multicomponent domino [4+2]/[3+2] cycloadditions of nitroheteroaromatics: an efficient synthesis of fused nitrogenated polycycles. Org Lett 9:4159–4162
Knoelker H-J (1995) Transition metal-mediated synthesis of carbazole derivatives. Adv Nitrogen Heterocycl 1:173–204
Pindur U, Erfanian-Abdoust H (1989) Indolo-2, 3-quinodimethanes and stable cyclic analogs for regio- and stereocontrolled syntheses of [b]-annelated indoles. Chem Rev 89:1681–1689
Collier SJ, Storr RC (1998) Heterocyclic ortho-quinodimethanes. Prog Heterocycl Chem 10:25–48
Terzidis M, Tsoleridis CA et al (2005) Chromone-3-carboxaldehydes in Diels–Alder reactions with indole-ortho-quinodimethane. Synthesis of tetrahydrochromeno[2, 3-b]carbazoles. Tetrahedron Lett 46:7239–7242
Terzidis MA, Tsoleridis CA et al (2008) Synthesis of chromeno[2,3-b]carbazole and chromeno[3,2-f]indazole derivatives. A new class of indole- and pyrazole-fused polycyclic compounds using o-quinodimethane chemistry. A reactivity and regioselectivity computational study. ARKIVOC 132–157
Tsoleridis CA, Dimtsas J et al (2006) Reactivity and regioselectivity in the synthesis of spiroindoles via indole o-quinodimethanes. An experimental and computational study. Tetrahedron 62:4232–4242
Diker K, De Maindreville MD et al (1999) Synthesis and resolution of a C2-symmetrical indolo-2, 3-quinodimethane dimer. Tetrahedron Lett 40:7459–7462
Diker K, De Maindreville MD et al (1999) The gramine route to the Diels–Alder adducts of indolo-2, 3-quinodimethanes. Tetrahedron Lett 40:7463–7467
Rao MVB, Satyanarayana J et al (1995) Anionic [4 + 2] cycloaddition reactions of indole-2, 3-dienolate with dienophiles: a facile regiospecific route to substituted carbazoles. Tetrahedron Lett 36:3385–3388
Laronze M, Sapi J (2002) 3-Cyanomethyl-2-vinylindoles as thermal indole-2, 3-quinodimethane equivalents: synthesis of functionalized 1, 2, 3, 4-tetrahydrocarbazoles. Tetrahedron Lett 43:7925–7928
Fuwa H, Sasaki M (2007) A new method for the generation of indole-2,3-quinodimethanes and 2-(N-alkoxycarbonylamino)-1,3-dienes. Intramolecular Heck/Diels–Alder cycloaddition cascade starting from acyclic a-phosphoryloxy enecarbamates. Chem Commun 2876–2878
Kuroda N, Takahashi Y et al (2006) A novel generation of indole-2, 3-quinodimethanes. Org Lett 8:1843–1845
Inagaki F, Mizutani M et al (2009) Generation of N-(tert-Butoxycarbonyl)indole-2, 3-quinodimethane and Its [4+2]-Type Cycloaddition. J Org Chem 74:6402–6405
Royer D, Wong Y-S et al (2008) Diastereodivergence and appendage diversity in the multicomponent synthesis of aryl-pyrrolo-tetrahydrocarbazoles. Tetrahedron 64:9607–9618
Cochard F, Laronze M et al (2004) Synthesis of carbazoles by a balanced four-component condensation. Tetrahedron Lett 45:1703–1707
Gribble GW (2003) Novel chemistry of indole in the synthesis of heterocycles. Pure Appl Chem 75:1417–1432
Gribble GW, Saulnier MG et al (2005) Novel indole chemistry in the synthesis of heterocycles. Curr Org Chem 9:1493–1519
Gribble GW, Keavy DJ et al (1992) Syntheses and Diels–Alder cycloaddition reactions of 4H-furo[3, 4-b]indoles. A regiospecific Diels–Alder synthesis of ellipticine. J Org Chem 57:5878–5891
Diaz MT, Cobas A, et al (1998) Polar control of the regioselectivity of hetaryne cycloadditions. Synthesis of ellipticine. Synlett. 157.
Kappe CO, Padwa A (1996) A facile and efficient synthesis of thieno[2, 3-c]furans and furo[3, 4-b]indoles via a Pummerer-induced cyclization reaction. J Org Chem 61:6166–6174
Zhang J, Zhang Y et al (2006) Coupling of N-heterocycle-fused enyne aldehydes with g, d-unsaturated Fischer carbene complexes. Organometallics 25:1279–1284
Jeevanandam A, Srinivasan PC (1995) Synthesis and cycloaddition of 2,4-dihydropyrrolo[3,4-b]indoles. J Chem Soc, Perkin Trans 1 2663–2665
Diaz M, Cobas A et al (2001) Synthesis of ellipticine by hetaryne cycloadditions – control of regioselectivity. Eur J Org Chem 4543–4549
Van Broeck PI, Van Doren PE, et al (1992) Diels–Alder reactions of pyrano[3,4-b]indol-3-ones and a 2-benzopyran-3-one with hetero substituted olefins: generation of carbazole and naphthalene derivatives by elimination instead of dehydrogenation. J Chem Soc, Perkin Trans 1 415–419
Bates RW, Pratt AJ et al (1998) Diels–Alder reactions of 1, 1-bis(methylthio)ethene with pyran-2-ones. Aust J Chem 51:383–387
Haider N, Kaferbock J et al (1999) Diels–Alder reaction of pyrano[3, 4-b]indolones with an electron-deficient pyridazinone: a new pathway to carbazole-fused pyridazines. Heterocycles 51:2703–2710
Chou TS, Tso HH (1989) Use of substituted 3-sulfolenes as precursors for 1, 3-butadienes. Org Prep Proced Int 21:257–296
Ko C-W, Chou T-s (1998) Preparation and reactions of benzofurano-, indolo-, and benzothieno-3-sulfolenes. J Org Chem 63:4645–4653
Kinsman AC, Snieckus V (1999) Directed ortho metalation-cross coupling route to indolo-4, 5-quinodimethanes. Synthesis of benz[e]indoles. Tetrahedron Lett 40:2453–2456
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2010 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Kester, R.F., Berthel, S.J., Firooznia, F. (2010). [4+2] Cycloaddition Reactions of Indole Derivatives. In: Gribble, G. (eds) Heterocyclic Scaffolds II:. Topics in Heterocyclic Chemistry, vol 26. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2010_55
Download citation
DOI: https://doi.org/10.1007/7081_2010_55
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-15732-5
Online ISBN: 978-3-642-15733-2
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)