Literature DB >> 28791530

Synthesis of diverse N-acyl-pyrazoles via cyclocondensation of hydrazides with α-oxeketene dithioacetal.

Bruna Á Pereira1, Alcione V de Bastos1, Wystan K O Teixeira1, Sidnei Moura E Silva2, Alex F C Flores1, Darlene C Flores3.   

Abstract

An elegant, efficient, and highly regioselective approach for the synthesis of novel methyl 5-amino-3-(methylthio)-1-differently substituted-1H-pyrazole-4-carboxylates is reported. The procedure involves the cyclocondensation of α-oxeketene S, S-dimethyl acetal building blocks with different alkyl, aryl, and heterocyclic acid hydrazides. The novel molecules were obtained in good yields and their identities confirmed by NMR and HRMS spectrometry.

Entities:  

Keywords:  Heterocycles; Hydrazides; Itaconic acid; Oxeketene; Pyrazoles; Pyrrolidinones

Mesh:

Substances:

Year:  2017        PMID: 28791530     DOI: 10.1007/s11030-017-9771-6

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   2.943


  7 in total

1.  Regioselective synthesis of 1-aryl-3,4-substituted/annulated-5-(methylthio)pyrazoles and 1-aryl-3-(methylthio)-4,5-substituted/annulated pyrazoles.

Authors:  S Peruncheralathan; T A Khan; H Ila; H Junjappa
Journal:  J Org Chem       Date:  2005-11-25       Impact factor: 4.354

Review 2.  From 2000 to mid-2010: a fruitful decade for the synthesis of pyrazoles.

Authors:  Santos Fustero; María Sánchez-Roselló; Pablo Barrio; Antonio Simón-Fuentes
Journal:  Chem Rev       Date:  2011-08-01       Impact factor: 60.622

3.  Acid hydrazides, potent reagents for synthesis of oxygen-, nitrogen-, and/or sulfur-containing heterocyclic rings.

Authors:  Poulomi Majumdar; Anita Pati; Manabendra Patra; Rajani Kanta Behera; Ajaya Kumar Behera
Journal:  Chem Rev       Date:  2014-02-07       Impact factor: 60.622

4.  Formal [4 + 1] Annulation of α-Arylhydrazonoketones and Dimethylsulfoxonium Methylide: One-pot Synthesis of Substituted Pyrazoles and Dihydropyrazoles.

Authors:  Qian Zhang; Mangfei Yu; Jingwen Yuan; Rui Zhang; Yongjiu Liang; Jiamei Tian; Dewen Dong
Journal:  J Org Chem       Date:  2016-06-30       Impact factor: 4.354

Review 5.  Recent advances in bioactive pyrazoles.

Authors:  Ş Güniz Küçükgüzel; Sevil Şenkardeş
Journal:  Eur J Med Chem       Date:  2014-12-05       Impact factor: 6.514

6.  Highly regioselective synthesis of 1-aryl-3 (or 5)-alkyl/aryl-5 (or 3)-(N-cycloamino)pyrazoles.

Authors:  S Peruncheralathan; A K Yadav; H Ila; H Junjappa
Journal:  J Org Chem       Date:  2005-11-11       Impact factor: 4.354

7.  Chemistry of Ketene N,S-Acetals: An Overview.

Authors:  Lin Zhang; Jinhuan Dong; Xianxiu Xu; Qun Liu
Journal:  Chem Rev       Date:  2016-01-13       Impact factor: 60.622

  7 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.