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Synthesis of 1-methyl-, 4-nitro-, 4-amino-and 4-iodo-1,2-dihydro-3H-pyrazol-3-ones

✍ Scribed by Y. C. Fiamegos; G. A. Pilidis; G. Varvounis

Publisher
Journal of Heterocyclic Chemistry
Year
2001
Tongue
English
Weight
44 KB
Volume
38
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

4‐Aminopyrazole‐3‐ones 4b, e, f were prepared from pyrazole‐3‐ones 1b‐d in a four‐step reaction sequence. Reaction of the latter with methyl p‐toluenesulfonate gave 1‐methylpyrazol‐3‐ones 2b‐d. Compounds 2b‐d were treated with aqueous nitric acid to give 4‐nitropyrazol‐3‐ones 3b‐d. Reduction of compounds 3b‐d by catalytic hydrogenation with Pd‐C afforded the 4‐amino compounds 4b, e, f. Using similar reaction conditions, nitropyrazole‐3‐ones derivatives 2c, d were reduced into aminopyrazole‐3‐ones 5e, f. 4‐Iodopyrazole‐3‐ones 7a, 7c and 8 were prepared from the corresponding pyrazol‐3‐ones 2a, 2c and 6 and iodine monochloride or sodium azide and iodine monochloride.

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