A convenient synthesis of 1,2,3,4,6,7,12,12b-octahydroindolo-[2,3-a]quinolizine

Autor:	Kunie Nagashima, Keiko Nakayama, Mayumi Yamauchi, Etsuji Yamanaka, Shin-ichiro Sakai, Noriko Yanagishima
Rok vydání:	1980
Předmět:	Tryptamine Pictet–Spengler reaction Indole alkaloid Quinolizine General Chemistry General Medicine Alkali metal chemistry.chemical_compound Malonate chemistry Drug Discovery Lactam Organic chemistry Ethyl group
Zdroj:	Chemical and Pharmaceutical Bulletin. 28:2527-2530
ISSN:	1347-5223 0009-2363
DOI:	10.1248/cpb.28.2527
Popis:	A convenient synthesis of 1, 2, 3, 4, 6, 7, 12, 12b-octahydroindolo [2, 3-a] quinolizine (1) is described. The condensation of tryptamine (2) with diethyl (2-formylethyl) malonate (3a), followed by treatment with alkali, gave the lactam ester (5a). Decarbethoxylation of 5a with LiCl-H2O-Me2SO afforded the lactam (8a), which was reduced with LiAlH4 to give the indoloquinolizine (1). The lactam (8b) which has an ethyl group at C3 was prepared from tryptamine (2) and diethyl ethyl (2-formylethyl) malonate (3b) instead of 3a.
Databáze:	OpenAIRE
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