Regioselective synthesis of N1-substituted-4-nitropyrazole-5-carboxylates the cyclocondensation of ethyl 4-(dimethylamino)-3-nitro-2-oxobut-3-enoate with substituted hydrazines

A simple and expeditious method for the regioselective synthesis of N1-substituted-4-nitropyrazole-5-carboxylates was developed. The method involves cyclocondensation of ethyl 4-(dimethylamino)-3-nitro-2-oxobut-3-enoate with a series of monosubstituted hydrazines to give N1-substituted-4-nitropyrazo...

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Published inOrganic & biomolecular chemistry Vol. 2; no. 48; pp. 9746 - 9752
Main Authors Zhao, Rulin, Hong, Zhenqiu, Wang, Bei, Kempson, James, Cornelius, Lyndon, Li, Jianqing, Li, Yi-Xin, Mathur, Arvind
Format Journal Article
Published 14.12.2022
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Summary:A simple and expeditious method for the regioselective synthesis of N1-substituted-4-nitropyrazole-5-carboxylates was developed. The method involves cyclocondensation of ethyl 4-(dimethylamino)-3-nitro-2-oxobut-3-enoate with a series of monosubstituted hydrazines to give N1-substituted-4-nitropyrazole-5-carboxylates with excellent regioselectivity and good yields. Solvent effects on regioselectivity of the cyclocondensation were examined. A simple and expeditious method for the regioselective synthesis of N1-substituted-4-nitropyrazole-5-carboxylates 2 was developed with excellent regioselectivity and good yields.
Bibliography:https://doi.org/10.1039/d2ob02006h
Electronic supplementary information (ESI) available: Copies of the 1H, 13C and 2D NMR spectra of all products. See DOI
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob02006h