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A facile synthesis of 1‐alkylthio and acylthio‐2,3‐dihydro‐1 H ‐naphtho[2,1‐ b ]thiopyrans and 4‐alkylthio and acylthio‐3,4‐dihydro‐2 H ‐naphtho[1,2‐ b ]thiopyrans
Author(s) -
Nakazawa Toshikatsu,
Itabashi Kunio
Publication year - 1988
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.5570250150
Subject(s) - chemistry , propionaldehyde , yield (engineering) , thio , sulfuric acid , medicinal chemistry , stereochemistry , organic chemistry , aldehyde , catalysis , materials science , metallurgy
The reaction of 3‐(2‐naphthylthio)propionaldehyde ( 3 )and its (1‐naphthylthio)isomer (7)with a variety of thiols and thio acids in the presence of sulfuric acid at room temperature afforded 1‐alkylthio and acylthio‐2,3‐dihydro‐1 H ‐naphtho[2,1‐ b ]thiopyrans 5 and 4‐alkylthio and acylthio‐3,4‐dihydro‐2 H ‐naphtho[1,2‐ b ]thiopyrans 9 in excellent yield.