Summary
We report here the synthesis of biheterocyclicα-amino acids by 1,3 dipolar cycloaddition of acetylenic compounds onα-azidoα-amino esters.
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References
Achamlale S, Elachqar A, Elhajji S, El hallaoui A, Roumestant ML, Viallefont Ph (1997) Synthesis ofα-triazolelα-amino acid derivatives. Amino Acids 12: 257–263
Alami A, El Hallaoui A, Elachqar A, Roumestant ML, Viallefont Ph (1996) The use of 5-substituted tetrazoles in a Synthesis of heterocyclicα-amino esters. Bull Soc Chim Belg 105: 769–771
Antonowa A, Hauptmann S (I976) p-Toluensulfonic acid salts of oximes and their conversion into nitriles and tetrazoles. Z Chem 16: 17
Barlin GB, Batterham TJ (1967) The proton magnetic resonnance spectra of some diazoles, triazoles, and tetrazoles. J Chem Soc (B): 516–518
Birkofer L, Ritter A, Uhlenbravick H (1963) Substitution and addition reaktionen an silylierten acetylenen. Chem Ber 96: 3280–3288
Butler RN, Scott FL (1966) Methylation studies on arylidene-5-tetrazolylhydrazones. J Org Chem 31: 3182–3187
Elachqar A, El Hallaoui A, Roumestant ML, Viallefont Ph (1994) Synthesis of heterocyclicα-aminophosphonic acids. Synthetic Comm 24: 1279–1286
Elhajji S (1992) Thesis, FES, Mai
Henry RA (1951) Methylation of 5-phenyl-tetrazole. J Am Chem Soc 73: 4470
Henry RA, Finnegan WG (1954) Mono-alkylation of sodium 5-aminotetrazole in aqueous medium. J Am Chem Soc 76: 923–926
Huff L, Henry RA (1970) Alkylation of 5-substituted tetrazoles. J Med Chem 13: 777
Juby PF, Hudyma TW (1969) Preparation and antiinflammtory properties of some 1substituted 3-(5-tetrazolylmethyl)indoles and homologs. J Med Chem 12: 396
Kishore V, Parmar SS, Gildersleeve DL (1978) Synthesis of 2,5-disubstituted tetrazoles as possible antiinflammatory agents. J Heterocycl Chem 15: 1335–1338
L'abbe G (1969) Decomposition and addition reactions of organic azides. Chem Rev: 345–363
Lunn WHW, Schoepp DD, Calligaro DO, Vasileff RT, Heinz LJ, Salhoff CR, O'malley PJ (1992) D,L-Tetrazol-5-ylglycine, a highly potent NMDA agonist: its synthesis and NMDA receptor efficacy. J Med Chem 35: 4608–4612
Monn JA, valli MJ, True RA, Schoepp DD, Leander JD, Lodge D (1993) Synthesis and pharmacological characterization of L-trans-4-tetrazolylproline (LY 300020): systematically-active AMPA receptor agonist. Bioorg Med Chem Lett 3: 95–98
Padwa A, Nahm S, Sato E (1978) Intramolecular 1,3-dipolar cycloaddition reaction of alkylenyl-substituted nitrile imines. J Org Chem 43: 1664–1670
Raap R, Howard J (1969) Tetrazolyl acetic acids. Can J Chem 47: 813–819
Schoepp DD, Smith CL, Lodge D, Millar JD, Leander JD, Sacaan Al, Lunn WHW (1992) D,L-(Tetrazol-5-yl)glycine: a novel and highly potent NMDA receptor agonist. Eur J Pharmacol 203: 237–241
Scott FL, Butler RN, Feeney J (I967) Proton magnetic resonance spectra of methylated 5-aminotetrazole derivatives. J Chem Soc (B): 919–920
Tsypin GI, Timofeeva TN, Mel'nikov VV, Gidaspov BV (1977) Structure and reactivity of aliphatic azido compounds. Isomeric composition of the products from cycloaddition of aliphatic azides to acetylene derivatives. Zh Org Khim 13: 2275–2281
Tsypin GI, Mel'nikov VV, Timofeeva TN, Gidaspov BV (1977) Structure and reactivity of aliphatic azido compounds. kinetics of the cycloaddition of alkylazides to acetylene derivatives. Zh Org Khim 13: 2281–2283
Zaïd F (1996) Thesis, FES, Juin
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Achamlale, S., Elachgar, A., El Hallaoui, A. et al. Synthesis of biheterocyclicα-amino acids. Amino Acids 17, 149–163 (1999). https://doi.org/10.1007/BF01361878
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DOI: https://doi.org/10.1007/BF01361878