Convenient synthesis of tert-butyl esters of indole-5-carboxylic acid and related heterocyclic carboxylic acids

Synthetic Communications

Volumn 36, Issue 21, 2006, Pages 3117-3123

  Fritsche, Alexandra ^a   Deguara, Heidrun ^a   Lehr, Matthias ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

1H Benzimidazole 5 carboxylic acid; 1H benzotriazole 5 carboxylic acid; Indole 5 carboxylic acid; Tert butyl ester; Tert butyl trichloroacetimidate

Indexed keywords

ACETIC ACID DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; BENZOFURAN DERIVATIVE; BENZOTHIOPHENE DERIVATIVE; BENZOTRIAZOLE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; HETEROCYCLIC CARBOXYLIC ACID; INDOLE DERIVATIVE; SODIUM HYDROXIDE;

AQUEOUS SOLUTION; ARTICLE; QUANTUM YIELD; REACTION ANALYSIS; SYNTHESIS;

EID: 33750205876     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910600907290     Document Type: Article

References (11)

1. Ludwig, J.; Lehr, M. Convenient synthesis of pyrrole- and indolecarboxylic acid tert-butylesters. Synth. Commun. 2004, 34, 3691-3695.
2. Widmer, U. A convenient preparation of t-butyl esters. Synthesis 1983, 135-136.
3. Inanaga, J.; Hirata, K.; Sacki, H.; Katsuki, T.; Yamaguchi, M. Rapid esterification by means of mixed anhydride and its application to large-ring lactonization. Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
4. Pozdnev, V. F. Activation of carboxylic acids with pyrocarbonates: Synthesis of t-butyl esters of N-protected amino acids from di t-butyl pyrocarbonate in the presence of pyridine and 4-dimethylaminopyridine. Khimii 1988, 58, 670-675.
5. Meth-Cohn, O. A simple, powerful, and efficient method for transesterification. J. Chem. Soc., Chem. Commun. 1986, 695-697.
6. Armstrong, A.; Brackenridge, I.; Jackson, R. F.W.; Kirk, J. M. A new method for the preparation of tertiary butyl ethers and esters. Tetrahedron Lett. 1988, 29, 2483-2486.
7. Zincke, T.; Helmert, B. About azimidouramidobenzoic acids and azimidobenzoic acids. Justus Liebigs Ann. Chem. 1896, 291, 313-342.
8. Tanaka, K.; Shimazaki, M.; Murakami, Y. Synthesis of N- acetylbenzimidazole derivatives. Chem. Pharm. Bull. 1982, 30, 2714-2722.
9. Phillips, M. A. The methylation of benziminazoles. J. Chem. Soc. 1931, 1143-1153.
10. Hirokawa, Y.; Yamazaki, H.; Yoshida, N.; Kato, S. A novel series of 6-methoxy-1H-benzotriazole-5-carboxamide derivatives with dual antiemetic and gastroprokinetic activities. Bioorg. Med. Chem. Lett. 1998, 8, 1973-1978.
11. Jacobi, S.; Hoffmann, H. Hydrolysis and oxidation of 1H-benzotriazole- carboxylic acid esters by rat liver microsomes. Arch. Pharm. 1990, 323, 825-827.