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Synthesis of the thia‐analog of angustidine, angustoline, naucléfine and nauéletine
Author(s) -
Shafiee A.,
Rashidbaigi A.
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.5570140805
Subject(s) - chemistry , pyridine , sodium hydride , medicinal chemistry , condensation , stereochemistry , thermodynamics , physics
Condensation of 1‐methyl‐3,4‐dihydrobenzo[ b ]thieno[2,3‐ c ]pyridine ( 6 ) with nicotinic acid in the presence of ynamine ( 12 ) gave 2‐nicotinyl‐1,2,3,4‐tetrahydro‐1‐methylenebenzo[ 6 ]thicno‐|2,3‐ c ]pyridine ( 13 ). Photocyclization of the enamide ( 13 ) afforded thia‐analog of naueléfine ( 15 ). Thia‐analogs of angustidine ( 19 ), and nauclétine ( 27 ) were prepared similary through photocyclization of the enamides 18 and 26 , respectively. Reduction of 27 with sodium boro‐hydride gave thia‐analog of angustoline ( 29 ).