Synthesis of nitro and amino  N ‐heterocycles  via  ring transformation of 2‐methyl‐3‐nitrochromone | Zendy

Takagi Kaname | Zendy; Tanaka Masaaki | Zendy; Murakami Yukitoshi | Zendy; Ogura Kuniyoshi | Zendy; Ishii Katsuyuki | Zendy; Morita Hikari | Zendy; Aotsuka Tomoji | Zendy

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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.

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