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
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.
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页数:8
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