Synthesis of ethyl N-(diphenyl)methyl-1,2,3,4- tetrahydroisoquinoline-3-carboxylates

Tetrahedron Letters

Volumn 38, Issue 40, 1997, Pages 6977-6980

  Mash, Eugene A ^a   Williams, Lawrence J ^a   Pfeiffer, Steven S ^a  

^a University of Arizona ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TETRAHYDROISOQUINOLINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS;

EID: 0030843899     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01668-7     Document Type: Article

References (16)

1. For examples, see Kametani, T. The Total Syntheses of Isoquinoline Alkaloids. In The Total Synthesis of Natural Products, vol. 3; ApSimon, J., Ed. John Wiley: New York, 1977; pp. 1-272.
2. (a) Hruby, V. J. Biopolymers 1993, 33, 1073-1082.
3. (b) Liskamp, R. M. J. Recl. Trav. Chim. Pays-Bas. 1994, 113, 1-19.
4. Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650.
5. (a) Whaley, W. M; Govindachari, T. R. Org. React., VI, 74-150 (1951).
6. (b) Whaley, W. M; Govindachari, T. R. Org. React., VI, 151-190 (1951).
7. Gensler, W. J. Org. React., VI, 191-206 (1951).
8. Jones, G. Pyridines and their Benzo Derivatives: (v) Synthesis. In Comprehensive Heterocyclic Chemistry, vol. 2; Boulton, A. J. and McKillop, A., Eds. Pergamon: New York, 1984; pp. 395-510.
9. Kuki, A.; Kotha, S. Tetrahedron Lett. 1992, 33, 1565-1569.
10. To the best of our knowledge, this synthesis of THIQ derivatives has not been reported. For previous alkylations of benzophenone imines for the synthesis of α-amino acids, see O'Donnell, M. J.; Wu, S.; Huffman, J. C Tetrahedron 1994, 50, 4507-4518 and references cited therein.
11. For related synthetic approaches to THIQ derivatives, see (a) Seebach, D.; Dziadulewicz, E.; Behrendt, L.; Cantoreggi, S.; Fitzi, R. Liebigs Ann. Chem. 1989, 1215-1232.
12. (b) Kammermeier, B. O. T.; Lerch, U.; Sommer, C. Synthesis 1992, 1157-1160.
13. (a) Eck, G.; Julia, M.; Pfeiffer, B.; Rolando, C. Tetrahedron Lett. 1985, 26, 4225-4228.
14. (b) Box, V. G. S.; Yiannikouros, G. P. Heterocycles 1990, 31, 1261-1270.
15. Heffner, R. J.; Joullié, M. M. Synthetic Communic. 1991, 21, 1055-1069.
16. 2) 430.2038, observed 430.2030.