Preparation of 1,2,3,4-tetrahydroisoquinolines lacking electron donating groups - An intramolecular cyclization complementary to the Pictet-Spengler reaction

Tetrahedron Letters

Volumn 37, Issue 31, 1996, Pages 5453-5456

  Stokker, G E ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TETRAHYDROISOQUINOLINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030605881     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01192-6     Document Type: Article

References (7)

1. 1. Austel, V.; Eisert, W.; Himmelsbach, F.; Linz, G.; Mueller, T.; Pieper, H.; Weisenberger, J. Eur. Pat. 528 369 A2 (1992).
2. 2. Kametani, T. J.; Fukumoto, K. Chem. Heterocycl. Compd. 1981, 38(1), 139-274.
3. 3. Zaugg, H. E., Synthesis 1984, 2, 85-110.
4. 3NO (M+H), 297.
5. 3 (M+H): 288.
6. 3, TMS) δ 2.96 (2H, t, J = 8 Hz), 3.65 (2H, q, J = 8 Hz), 3.92 (3H, s), 7.28 (2H, d, J = 7.8 Hz), 8.02 (2H, d, J = 7.8 Hz).
7. 7. Starting methyl ester was prepared by Pd(0) catalyzed carbonylmethylation of the corresponding iodide which was prepared as in Kajigaeshi, S., Kakinami, T., Moriwaki, M., Watanabe, M., Fugisaki, S., Okamoto, T. Chem. Lett. 1988, 5, 795.