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Intramolecular substitution of unactivated aryl groups by thioamide anion
Author(s) -
Spitulnik M. J.
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.5570140626
Subject(s) - chemistry , thioamide , intramolecular force , aryl , medicinal chemistry , ring (chemistry) , nucleophilic substitution , amide , azine , organic chemistry , alkyl
The general reaction of intramolecular nucleophilic substitution of unactivated aryl groups by thioamide anion in dipolar aprotic amide solvent is extended by the syntheses of 6‐chloro‐5‐methoxy‐2‐methylbenzothiazole from 2′,4′‐dichloro‐5′‐methoxythioacetanilide and 6‐methoxy‐2‐methylbenzothiazole from 4′‐methoxy‐2′‐nitrothioacetanilide. The six‐membered fused ring heterocycles, 2‐methyl‐4 H ,3‐benzothiazine and 6,8‐dichloro‐3‐rnethyl‐1 H ‐4,1,2‐benzothiadi‐azine are also prepared.