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Synthesis in the diazasteroid group VI. A synthesis of 2,3‐dimethoxy‐15‐methyl‐8,15‐diazaestra‐1,3,5(10)triene
Author(s) -
Yamazaki Takao,
Nagata Masanori,
Matoba Katsuhide,
Takahata Hiroki,
Castle Raymond N.
Publication year - 1977
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570140323
Subject(s) - chemistry , quinolizidine , amide , ring (chemistry) , derivative (finance) , stereochemistry , group (periodic table) , medicinal chemistry , organic chemistry , alkaloid , financial economics , economics
Homoveratrylamine (II) was condensed with 3‐(2‐carbomethoxyethyl)‐1,3‐dimethyl‐2‐pyrrol‐idone (Ib) to furnish the corresponding amide (III), which was subjected to the Bischler‐Napieralski reaction to afford the corresponding dihydroisoquinoline derivative (IV). Compound V was obtained by the reductive ring closure of Vila which was obtained by the hydrogena‐tion of IV. The stereochemistry of V is proposed to have the anti‐trans‐trans quinolizidine conformation.