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Synthesis of nitro and amino N ‐heterocycles via ring transformation of 2‐methyl‐3‐nitrochromone
Author(s) -
Takagi Kaname,
Tanaka Masaaki,
Murakami Yukitoshi,
Ogura Kuniyoshi,
Ishii Katsuyuki,
Morita Hikari,
Aotsuka Tomoji
Publication year - 1987
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.5570240420
Subject(s) - chemistry , isoxazole , hydroxylamine , nitro , ring (chemistry) , pyrrole , pyrazole , pyrimidine , medicinal chemistry , catalysis , stereochemistry , organic chemistry , alkyl
2‐Methyl‐3‐nitrochromone ( 1 ) reacted with acid hydrazides, S ‐methylisothiourea, hydroxylamine and ethyl aminoethanoate to give the nitro derivatives of pyrazole 2 , pyrimidine 6 , isoxazole 11 and pyrrole 13 , respectively. These nitro compounds were reduced by catalytic hydrogenation to the corresponding amino derivatives. In the case of 2 , a rearrangement of the acyl group took place during the reduction. Substitution reactions of the 2‐methylthio group in 6 were also described.