Modular Synthesis of 3,6-Disubstituted-1,2,4-triazines via the Cyclodehydration of ß-Keto- N-acylsulfonamides with Hydrazine Salts.

Dowling, Matthew S; Jiao, Wenhua; Hou, Jie; Jiang, Yuchun; Gong, Shangsheng

Dowling, Matthew S; Jiao, Wenhua; Hou, Jie; Jiang, Yuchun; Gong, Shangsheng.

Afiliación

Dowling MS; Medicine Design, Pfizer Inc. , Eastern Point Road , Groton , Connecticut 06340 , United States.
Jiao W; Medicine Design, Pfizer Inc. , Eastern Point Road , Groton , Connecticut 06340 , United States.
Hou J; WuXi AppTec , 288 Fute Zhong Road, Waigaoqiao Free Trade Zone , Shanghai 200131 , China.
Jiang Y; WuXi AppTec , 288 Fute Zhong Road, Waigaoqiao Free Trade Zone , Shanghai 200131 , China.
Gong S; WuXi AppTec , 288 Fute Zhong Road, Waigaoqiao Free Trade Zone , Shanghai 200131 , China.

J Org Chem ; 83(7): 4229-4238, 2018 04 06.

Article en En | MEDLINE | ID: mdl-29514458

RESUMEN

A straightforward method for preparing 3,6-disubstituted-1,2,4-triazines through a redox-efficient cyclodehydration of ß-keto- N-acylsulfonamides with hydrazine salts is described. Two approaches for synthesizing the requisite ß-keto- N-acylsulfonamides are presented, which allow for the late stage incorporation of either the C3 or C6 substituent in a flexible manner from acid chlorides or α-bromoketones, respectively. The scope of this methodology includes primary and secondary sp3-linked substituents at both the C3 and C6 positions, and the mild reaction conditions tolerate a variety of sensitive functionalities.

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: J Org Chem Año: 2018 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Estados Unidos

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