Abstract
The fusion of a benzene ring with five-membered aromatic heterocycles (π-excessive pyrrole, furan and thiophene) results in benzo[a], benzo[b] and benzo[c] fused heterocycles depending on the annelation of the benzene ring on to the ‘face a’ (1,2-bond), ‘face b’ (2,3-bond) and ‘face c’ (3,4-bond), respectively.
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References
R. J. Sundberg, The Chemistry of Indoles, Academic Press, New York, 1970 and 1971.
W. J. Houlihan (Ed.), Chem. Heterocycl. Compd. 25–1 and 25–2 (1972); 253 (1979).
R. J. Sundberg in A. R. Katritzky and C. W. Rees (Eds.), Comprehensive Heterocyclic Chemistry Vol. 4, Pergamon Press, Oxford, 1984, pp. 313.
D. J. Chadwick in A. R. Katritzky and C. W. Rees (Eds.), Comprehensive Heterocyclic Chemistry Vol. 4, Pergamon Press, Oxford, 1984, pp. 155.
R. A. Jones in A. R. Katritzky and C. W. Rees (Eds.), Comprehensive Heterocyclic Chemistry Vol. 4, Pergamon Press, Oxford, 1984, pp. 201.
R. J. Sundberg in H. Suschitzky and E. F. V. Scriven (Eds.), Progress in Heterocyclic Chemistry Vols. 1–6 Pergamon Press, Oxford, 1989–1994.
U. Pindur and R. Adam, J. Heterocycl. Chem. 25, 1 (1988); M. A. Yuroskaya, Khim. Geterotsikl. Soedin. 23, 1155 (1987); L. S. Hegedus, Angew. Chem. Int. Ed. Engl. 27, 113 (1988); R. M. Acheson, Adv. Heterocycl. Chem. 51, 105 (1990).
R. J. Sundberg, The Chemistry of Indoles, Academic Press, New York, 1970, pp. 176.
R. K. Brown in W. J. Houlihan (Ed.), Chem. Heterocycl. Compd. 25–1, 396 (1972).
R. J. Sundberg, The Chemistry of Indoles, Academic Press, New York, 1970, pp. 182.
R. K. Brown in W. J. Houlihan (Ed.), Chem. Heterocycl. Compd. 25–1, 479 (1972).
R. L. Augustine, A. J. Gustaysen, S. F. Wanat, I. C. Pattison, K. S. Houghton and G. Koletar, J. Org . Chem. 38, 3004 (1973).
E. Ucciani and A. Bonfand, J. Chem. Soc. Chem. Commun. 82 (1981).
T. Sakamoto, Y. Kondo and H. Yamanaka, Heterocycles 27, 2225 (1988); L. S. Hegedus, G. F. Allen and E. L. Waterman, J. Am. Chem. Soc. 98, 2674 (1976).
Y. Ito, K. Kobayashi and T. Saegusa, J. Am. Chem. Soc. 99, 3532 (1977); Y. Ito, K. Kobayashi, N. Seko and T. Saegusa, Chem. Lett. 1273 (1979); Y. Ito, K. Kobayashi and T. Saegusa, J. Org . Chem. 44, 2030 (1979).
R. K. Brown in W. J. Houlihan (Ed.), Chem. Heterocycl. Compd. 25–1, 317 (1972).
B. Robinson, Chem. Rev. 63, 373 (1963); 69, 227 (1969).
B. Robinson, The Fischer-Indole Synthesis, Wiley, New York, 1982.
R. J. Sundberg, The Chemistry of Indoles, Academic Press, New York, 1970, pp. 142.
R. K. Brown in W. J. Houlihan (Ed.), Chem. Heterocycl. Compd. 25–1, 232 (1972).
F. M. Miller and W. N. Schinske, J. Org . Chem. 43, 3384 (1978).
R. R. Phillips, Org. React. 10, 143 (1959).
P. G. Gassman, T. J. van Bergen, D. P. Gilbert and B. W. Cue, Jr., J. Am. Chem. Soc. 96, 5495 (1974).
R. A. Jones, M. T. P. Marriott, W. P. Rosenthal and J. S. Arques, J. Org . Chem. 45, 4515 (1980).
R. A. Jones and J. S. Arques, Tetrahedron 37, 1597 (1981).
K. Isomura, S. Kobayashi and H. Taniguchi, Tetrahedron Lett. 3499 (1968).
T. Nishiwaki, K. Azechi and F. Fujiyama, J. Chem. Soc. Perkin Trans. 1, 1867 (1974).
K. Isomura, K. Uto and H. Taniguchi, J. Chem. Soc. Chem. Commun. 664 (1977).
W. A. Remers in W. J. Houlihan (Ed.), Chem. Heterocycl. Compd. 25–1, 1 (1972).
D. M. Muir and M. C. Whiting, J. Chem. Soc. Perkin Trans. 2, 1316 (1975).
H. Ishii, K. Murakami, Y. Murakami and K. Hosoya, Chem. Pharm. Bull. 25, 3122 (1977).
K. Rush in W. J. Houlihan (Ed.), Chem. Heterocycl. Compd. 25–2, 537 (1972).
H. F. Hodson and G. F. Smith, J. Chem. Soc. 3546 (1957); W. E. Noland, L. R. Smith and K. R. Rush, J. Org . Chem. 30, 3457 (1965).
B. C. Challis and A. J. Lawson, J. Chem. Soc. Perkin Trans. 2, 918 (1973).
K. L. Erikson, M. R. Brennan and P. A. Namnum. Synth. Commun. 11, 253 (1981).
R. J. Sundberg, The Chemistry of Indoles, Academic Press, New York, 1970, Chapter 1.
M. De Rosa, L. Carbognani and A. Febres, J. Org. Chem. 46, 2054 (1981).
M. De Rosa and J. L. T. Alonso, J. Org . Chem. 43, 2639 (1978).
V. Bocchi and G. Palla, Synthesis, 1096 (1982).
J. C. Powers, Chem. Heterocycl. Compd. 25–2, 127 (1972).
W. A. Remers, Chem. Heterocycl. Compd. 25–3, 357 (1979).
G. F. Smith and D. A. Taylor, Tetrahedron 29, 669 (1973).
A. P. Terent’ev, S. K. Golubeva and L. V. Tsymbal, Zh. Obshch. Khim. 19, 781 (1949).
R. S. Alexander and A. R. Butler, J. Chem. Soc. Perkin Trans. 2, 696 (1976).
R. A. Jones and G. P. Bean, The Chemistry of Pyrroles, Academic Press, London, 1977, Chapter 4.
S. Swaminathan and S. Ranganathan, J. Org . Chem. 22, 70 (1957).
F. G. Bordwell, G. E. Drucker and H. E. Fried, J. Org . Chem. 46, 632 (1981).
R. W. Franck, K. Miyano and J. F. Blount, Heterocycles 9, 807 (1978).
K. J. Baird, M. F. Grundon, D. M. Harrison and M. G. Magee, Heterocycles 15, 713 (1981).
G. Malesami, G. Chiarelotto, M. G. Ferlin and S. Masiero, J. Heterocycl. Chem. 18, 613 (1981).
M. M. Cooper, G. J. Hignett, R. F. Newton, J. A. Joule, M. Harris and J. D. Hinchley, J. Chem. Soc. Chem. Commun. 432 (1977).
D. A. Taylor, M. M. Baradarani, S. J. Martinez and J. A. Joule, J. Chem. Res. (S) 387 (1979).
W. R. Ashcroft, M. G. Beal and J. A. Joule, J. Chem. Soc. Chem. Commun. 994 (1981).
B. J. Clark and R. Graysham, J. Chem. Res. (S) 324 (1981).
R. A. Jones and G. P. Bean, The Chemistry of Pyrroles, Academic Press, London, 1977, Chapter 5.
R. Bonnett and S. A. North, Adv. Heterocycl. Chem. 29, 341 (1981).
G. W. Gribble, P. D. Lord, J. Skotnicki, S. E. Dietz, J. T. Eaton and J. L. Johnson, J. Am. Chem. Soc. 96, 7812 (1974).
J. G. Berger, Synthesis, 508 (1974).
G. W. Gribble and J. H. Hoffiman, Synthesis, 859 (1977).
J. G. Berger, F. Davidson and G. E. Langford, J. Med. Chem. 20, 600 (1977).
Y. Kikugawa, J. Chem. Res. (S) 184 (1978).
Y. Kikugawa, J. Chem. Res. (S) 212 (1977).
S. A. Monti and R. R. Schmidt, III, Tetrahedron 27, 3331 (1971).
J. Hutton and W. A. Waters, J. Chem. Soc. 4253 (1965).
Y. Kanaoka, M. Aiura and S. Hariya, J. Org . Chem. 36, 458 (1971).
R. M. Acheson and N. F. Elmore, Adv. Heterocycl. Chem. 23, 265 (1978).
K. Matsumoto, T. Uchida and R. M. Acheson, Heterocycles 16, 1367 (1981).
G. Seitz and T. Kampchen, Arch. Pharm. (Weinheim, Ger.) 309, 679 (1976).
P. D. Davis and D. C. Neckers, J. Org . Chem. 45, 456 (1980).
R. M. Acheson, J. N. Bridson and T. S. Cameron, J. Chem. Soc. Perkin Trans. 1, 968 (1972).
M. J. S. Dewar, A. J. Harget, N. Trinajastic and S. D. Worley, Tetrahedron 26, 4505 (1970).
E. Chacko, J. Bornstein and D. J. Sardella, Tetrahedron 35, 1055 (1979); R. P. Kreher, H. Hennige, M. Konrad, J. Uhrig and A. Clemens, Z. Naturforsch. 46, 89 (1991).
D. F. Veber and W. Lwowski, J. Am. Chem. Soc. 86, 4152 (1964).
B. Jaques and R. G. Wallace, Tetrahedron 33, 581 (1977).
J. C. Emmett and W. Lwowski, Tetrahedron 22, 1011 (1966).
M. J. Haddadin and N. C. Chelhot, Tetrahedron Lett. 5185 (1973).
R. Kreher and H. Hennige, Tetrahedron Lett. 1911 (1973).
R. Bonnett and R. F. C. Brown, J. Chem. Soc. Chem. Commun. 393 (1972).
R. Kreher and J. Seubert, Angew. Chem. Int. Ed. Engl. 3, 639 (1964); 5, 967 (1966); R. Kreher and G. Use, 19, 320 (1980).
S. H. Pine, Org. React. 18, 403 (1970).
R. Kreher and K. J. Herd, Angew. Chem. Int. Ed. Engl. 13, 739 (1974).
R. Kreher and K. J. Herd, Tetrahedron Lett. 1661 (1976)
R. Kreher and K. J. Herd, Heterocycles 11, 409 (1978).
L. J. Kricka and J. M. Vernon., J. Chem. Soc. Perkin Trans. 1, 904 (1972).
L. J. Kricka and J. M. Vernon, J. Chem. Soc. (C), 2667 (1971).
M. R. Bryce and J. M. Vernon, Adv. Heterocycl. Chem. 28, 183 (1981).
G. W. Gribble, R. W. Allen, C. S. Le Houillier, J. T. Eaton, N. R. Easton, Jr., R. I. Slayton and M. P. Sibi, J. Org . Chem. 46, 1025 (1981).
F. J. Swinbourne, J. H. Hunt and G. Klinkert, Adv. Heterocycl. Chem. 23, 103 (1978).
H. L. Blewitt in A. Weissberger and E. C. Taylor (Eds.), Special Topics in Heterocyclic Chemistry Vol. 30, Academic Press, New York, 1977, pp. 117.
E. E. Glover, K. D. Vaughan and D. C. Bishop, J. Chem. Soc. Perkin Trans. 1, 2595 (1973).
A. Kakehi, S. Ito, K. Watanabe, M. Kitagawa, S. Takeuchi and T. Hashimoto, J. Org . Chem. 45, 5100 (1980).
D. R. Bragg and D. G. Wibberley, J. Chem. Soc. 3277 (1963).
A. Crabtree, A. W. Johnson and J. C. Tebby, J. Chem. Soc. 3497 (1961).
W. Flitsch and E. Gerstmann, Chem. Ber. 102, 1309 (1969).
W. J. Lin, O. W. Webster and R. E. Benson, J. Am. Chem. Soc. 87, 3651 (1965).
T. Uchida and K. Matsumoto, Synthesis 209 (1976).
A. Kakehi and S. Ito, Bull. Chem. Soc. Japan 47, 938 (1974).
B. A. Hess, Jr., L. J. Schaad and C. W. Holyoke, Jr., Tetrahedron 28, 3657 (1972).
J. A. Hickman and D. G. Wibberley, J. Chem. Soc. Perkin Trans. 1, 2954 (1972).
G. Jones in N. V. Sidgwick, I. T. Millar and H. D. Springall (Eds.), The Organic Chemistry of Nitrogen, 3rd Edn., Clarendon Press, Oxford, 1966, pp. 752.
W. Flitsch and U. Kramer, Adv. Heterocycl. Chem. 22, 321 (1978).
J. A. Joule, Adv. Heterocycl. Chem. 35, 83 (1984); R. M. Acheson, 51, 105 (1990).
C. Paoletti, S. Cros, N. D. Xuong, P. Lecointe and A. Moisand, Chem. Biol. Interactions 25, 45 (1979); U. Pindur, M. Haber and K. Sattler, Pharmazie in Unserer Zeit 21, 21 (1992).
E. Campaigne and R. D. Lake, J. Org . Chem. 24, 478 (1959).
M. Julia and J. Lenzi, Bull. Soc. Chim. France, 2262 (1962).
B. Akermark, L. Eberson, E. Jonsson and E. Pettersson, J. Org . Chem. 40, 1365 (1975).
R. B. Miller and T. Moock, Tetrahedron Lett. 3319 (1980).
W. Carruthers, Chem. Commun. 272 (1966); D P Chakraborty, Tetrahedron Lett. 661 (1966).
K. H. Grellmann, W. Kuhnle, H. Weller and T. Wolffe, J. Am. Chem. Soc. 103, 6889 (1981).
J. I. G. Cadogan, M. Cameron-Wood, R. K. Mackie and R. J. G. Searle, J. Chem. Soc. 4831 (1965).
M. Sekine, H. Yamagata and T. Hata, Tetrahedron Leu. 375 (1979).
R. J. Sundberg, D. W. Gillispie and B. A. DeGraff, J. Am. Chem. Soc. 97, 6193 (1975).
R. B. Miller and J. G. Stowell, J. Org . Chem. 48, 886 (1983).
J. L. Bemeir, J. P. Henichart, C. Vaccher and R. Houssin. J. Org . Chem. 45, 1493 (1980).
J. Y. Lallemand, P. LeMaitre, L. Beeley, P. Lesca and D. Mansuy, Tetrahedron Lett. 1261 (1978).
A. H. Jackson, P. R. Jenkins and P. V. R. Shannon, J. Chem. Soc. Perkin Trans. 1, 1698 (1977).
J. B. Kyziol and A. Lyzniak, Tetrahedron 36, 3017 (1980).
A. Cipiciani, S. Clementi, P. Linda, G. Marino and G. Savelli, J. Chem. Soc. Perkin Trans. 2, 1284 (1977).
M. J. E. Hawkins, A. H. Jackson, A. M. Oliveira-Campos and P. V. R. Shannon, Chem. Ind. 338 (1981).
P. F. Schuda, Top. Curr. Chem. 91, 75 (1980).
D. R. Bender, J. E. Hearst and H. Rapoport, J. Org . Chem. 44, 2176 (1979).
P. Nore and E. Honkanen, J. Heterocycl. Chem. 17, 985 (1980).
R. F. C. Brown and C. M. Jones, Aust. J. Chem. 33, 1817 (1980).
A. Mustafa, Chem. Heterocycl. Compd. 29, 1 (1974).
P. Cagniant and D. Cagniant, Adv. Heterocycl. Chem. 18, 337 (1975).
D. M. X. Donnelly and M. J. Meegan in A. R. Katritzky and C. W. Rees (Eds.), Comprehensive Heterocyclic Chemistry Vol. 4, Pergamon Press, Oxford, 1984, pp. 657.
M. V. Sargent and F. M. Dean in A. R. Katritzky and C. W. Rees (Eds.), Comprehensive Heterocyclic Chemistry Vol. 4, Pergamon Press, Oxford, 1984, pp. 599.
C. W. Bird in H. Suschitzky and E. F. V. Scriven (Eds.), Progress in Heterocyclic Chemistry Vol. 6, Pergamon Press, Oxford, 1994, pp. 129.
J. K. MacLeod and B. R. Worth, Tetrahedron Lett. 237 (1972); J. K. Macleod, B. R. Worth and R. J. Wells, 241 (1972).
E. Bisagni and C. Rivalle, Bull. Soc. Chim. France, 2463 (1969).
M. L. Oftedahl, J. W. Baker and M. W. Dietrich, J. Org . Chem. 30, 296 (1965).
B. Holt and P. A. Lowe, Tetrahedron Lett. 683 (1966).
E. Baciocchi, S. Clementi and G. V. Sebastiani, J. Heterocycl. Chem. 14, 359 (1977).
J. Astoin, P. Demerseman, N. Platzer and R. Royer, J. Heterocycl. Chem. 14, 861 (1977).
M. G. Bartle, S. T. Gore, R. K. Mackie, S. Mhatre and J. M. Tedder, J. Chem. Soc. Perkin Trans. 1, 401 (1978).
M. Cugnon de Sevricourt and M. Robba, Bull. Soc. Chim. France, 142 (1977).
S. Gronowitz and T. Frejd, Chem. Heterocycl. Compd. 14, 353 (1978); H. W. Gschwend and H. R. Rodriguez, Org. React. 26, 1 (1979).
E. Wenkert, M. E. Alonso, H. E. Gottlieb, E. L. Sanchez, R. Pellicciari and P. Cogolli, J. Org . Chem. 42, 3945 (1979).
V. Zanker, Methoden Org. Chem. (Houben-Weyl) 4/5a, 552 (1975).
A. H. A. Tinnemans and D. C. Neckers, J. Org . Chem. 42, 2374 (1977)
D. C. Neckers and F. L. Wagenaar, J. Org . Chem. 46, 3939 (1981)
S. R. Ditto, P. D. ‘Davis and D. C. Neckers, Tetrahedron Lett. 521 (1981).
M. J. Haddadin, Heterocycles 9, 865 (1978).
W. Friedrichsen, Adv. Heterocycl. Chem. 26, 135 (1980); R. Rodrigo, Tetrahedron, 44, 2093 (1988).
B. Rickborn, Adv. Theor. Interesting Mol. 1, 1 (1989).
U. E. Wiersum and W. J. Mijs, J. Chem. Soc. Chem. Commun. 347 (1972); E. Chacko, D. J. Sardella and J. Bornstein, Tetrahedron Lett. 2507 (1976).
R. N. Warrener, J. Am. Chem. Soc. 93, 2346 (1971).
J. D. White, M. E. Mann, H. D. Kirshenbaum and A. Mitra, J. Org . Chem. 36, 1048 (1971).
F. J. Petracek, N. Sugisaka, M. W. Klohs, R. G. Parker, J. Bordner and J. D. Roberts, Tetrahedron Lett. 707 (1970).
J. G. Smith and R. B. McCall, J. Org . Chem. 45, 3982 (1980).
F. M. Dean and M. V. Sargent in A. R. Katritzky and C. W. Rees (Eds.), Comprehensive Heterocyclic Chemistry Vol. 4, Pergamon Press, Oxford, 1984, pp. 531.
B. G. Pring and N. E. Stjernstrom, Acta Chem. Scand. 22, 538 (1968).
S. Oae, K. Iida, K. Shinhama and T. Takata, Bull. Chem. Soc. Japan 54, 2374 (1981).
W. J. Davidson and J. A. Elix, Aust. J. Chem. 23, 2119 (1970).
B. Iddon and R. M. Scrowston, Adv. Heterocycl. Chem. 11, 177 (1970).
R. M. Scrowston, Adv. Heterocycl. Chem. 29, 171 (1981).
S. Rajappa in A. R. Katritzky and C. W. Rees (Eds.), Comprehensive Heterocyclic Chemistry Vol. 4, Pergamon Press, Oxford, 1984, pp. 741.
E. Campaigne in A. R. Katritzky and C. W. Rees (Eds.), Comprehensive Heterocyclic Chemistry Vol. 4, Pergamon Press, Oxford, 1984, pp. 863.
E. Campaigne and Y. Abe. J. Heterocycl. Chem. 12, 889 (1975)
N. B. Chapman, R. M. Scrowston and T. M. Sutton, J. Chem. Soc. Perkin Trans. 1, 3011 (1972).
A. J. Krubsack and T. Higa, Tetrahedron Lett. 125 (1973)
A. J. Krubsack, R. Sehgal, W. A. Loong and W. E. Slack, J. Org . Chem. 40, 3179 (1975).
K. Undheim and R. Lie, Acta Chem. Scand. 27, 595 (1973).
M. G. Reinecke, J. G. Newsom and L. J. Chen, J. Am. Chem. Soc. 103, 2760 (1981)
M. G. Reinecke, J. G. Newsom and K. A. Almqvist, Tetrahedron 37, 4151 (1981).
M. S. Raasch, J. Org . Chem. 45, 2151 (1980).
R. M. Acheson and M. W. Cooper, J. Chem. Soc. Perkin Trans. 1, 1185 (1980).
J. A. Cotruvo and I. Degani, Chem. Commun. 436 (1971).
P. Geneste, J. Grimaud, J. L. Olive and S. N. Ung, Tetrahedron Lett. 2345 (1975).
K. J. Brown and O. Meth—Cohn, Tetrahedron Lett., 4069 (1974).
E. Wenkert, T. W. Ferreira and E. L. Michelotti, J. Chem. Soc. Chem. Commun. 637 (1979).
P. Grandclaudon and A. Lablache—Combier, J. Org . Chem. 43, 4379 (1978).
D. N. Reinhoudt, Adv. Heterocycl. Chem. 21, 253 (1977).
D. C. Neckers, J. H. Dopper and H. Wynberg, J. Org . Chem. 35, 1582 (1970).
J. H. Dopper and D. C. Neckers, J. Org . Chem. 36, 3755 (1967); A. H. A. Tinnemans and D. C. Neckers, J. Org . Chem. 43, 2493 (1978).
T. Matsuo and S. Mihara, Bull. Chem. Soc. Japan 50, 1797 (1977).
B. Iddon, Adv. Heterocycl. Chem. 14, 331 (1972).
M. E. Mann and J. D. White, Chem. Commun. 420 (1969).
M. P. Cava, N. M. Pollack, O. A. Marner and M. J. Mitchell, J. Org . Chem. 36, 3932 (1971)
M. P. Cava, N. M. Pollack and G. A. Dieterle, J. Am. Chem. Soc. 95, 2558 (1973).
J. M. Holland and D. W. Jones, J. Chem. Soc. (C), 536 (1970).
R. Mayer, H. Kleinert, S. Richter and K. Gewald, J. Prakt. Chem. 20, 244 (1963).
G. Cignarella and G. Cordella, Tetrahedron Lett. 1871 (1973)
G. Cignarella, A. Nuvole and M. M. Curzu, Gazz. Chim. Ital. 111, 333 (1981)
G. Cignarella and G. Cordella, 104, 455 (1974).
E. Campaigne, L. Ergener and B. G. Heaton, J. Org . Chem. 27, 4111 (1962).
K. P. Zeller and H. Petersen, Synthesis, 532 (1975).
J. Ashby, M. Ayad and O. Meth—Cohn, J. Chem. Soc. Perkin Trans. 1, 1744 (1974).
J. Ashby and C. C. Cook, Adv. Heterocycl. Chem. 16, 181 (1974).
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Gupta, R.R., Kumar, M., Gupta, V. (1999). Benzo-Fused Five-Membered Heterocycles with One Heteroatom. In: Heterocyclic Chemistry. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-07757-3_3
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