Synthesis of 1,2,4-Triazoles and 1,3,4-Thiadiazinones by [3+2] and [3+3] Domino Annulation Reactions of Nitrile Imines with Succinimide and Thiazolidine-2,4-dione

被引：2

作者：

Chilaka, Sai Krishna ^{[1
,2
]}

Chinthapally, Krishna Prasad ^{[1
]}

Soda, Anil Kumar ^{[1
,2
]}

Chellu, Ramesh Kumar ^{[1
,2
]}

Kurva, Srinivas ^{[1
]}

Nanubolu, Jagadeesh Babu ^{[2
,3
]}

Madabhushi, Sridhar ^{[1
,2
]}

机构：

[1] CSIR Indian Inst Chem Technol, Fluoro & Agrochem Dept, Hyderabad 500007, India

[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India

[3] CSIR Indian Inst Chem Technol, Ctr Xray Crystallog, Hyderabad 500007, India

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 12卷 / 04期

关键词：

1; 2; 4-triazoles; 3; 4-thiadiazinones; nitrile imine; succinimide; domino annulation reaction; 1,3-DIPOLAR CYCLOADDITION; HYDRAZONOYL CHLORIDES; DERIVATIVES; TRIAZOLE; POTENT;

D O I：

10.1002/ajoc.202300041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein; we report protocols for the synthesis of 1,2,4-triazoles and 1,3,4- thiadiazinones by [3+2] and [3+3] domino annulation reactions of nitrile imines with succinimide and thiazolidine-2,4-dione, respectively, using a base (1.5 equivalents) and alcohol as a solvent. In these reactions, notably, alcohol serves not only as a solvent but also as a reactant participating in the formation of ester functionality in products. These methodologies provide metal-free and direct approaches to the synthesis of 1,2,4-triazoles and 1,3,4-thiadiazinones under mild conditions with a wide substrate scope and high yields.

引用

页数：8

共 52 条

[1] Synthesis, Antimicrobial, and Anti-inflammatory Activities of Novel 5-(1-Adamantyl)-4-arylideneamino-3-mercapto-1,2,4-triazoles and Related Derivatives [J].