A New Efficient Method for the Synthesis of Fused [1,2,5]Thiadiazoles and Their Dearomatization with C-Nucleophiles

被引：4

作者：

Fedorenko, Alexey K. ^{[1
]}

Ivanova, Victoria V. ^{[1
,2
]}

Minyaev, Mikhail E. ^{[1
]}

Bastrakov, Maxim A. ^{[1
]}

Starosotnikov, Alexey M. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Leninsky Prosp 47, Moscow 119991, Russia

[2] DI Mendeleev Univ Chem Technol Russia, Higher Chem Coll, RAS, Miusskaya sq 9, Moscow 125047, Russia

来源：

CHEMISTRYSELECT | 2023年 / 8卷 / 43期

关键词：

dearomatization; fused [1,2,5]thiadiazoles; nitrogen heterocycles; nucleophilic addition; ortho-diamines; SULFUR MONOCHLORIDE; DERIVATIVES; MOLECULES; DESIGN;

D O I：

10.1002/slct.202303122

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

General method for the annulation of [1,2,5]thiadiazole ring to pyridine and benzene cycle has been developed using sulfur monochloride as a sulfur source. On this basis a number of [1,2,5]thiadiazolo[4,3-b]pyridines and benzo[c]thiadiazoles were synthesized. The most pi-deficient [1,2,5]thiadiazolo[4,3-b]pyridines readily react with neutral carbon nucleophiles such as CH-acids, indoles, pyrrole and phloroglucinol to give 1,4-adducts. An efficient method for the synthesis of fused [1,2,5]thiadiazoles by the reaction of ortho-diaminopyridines and benzenes with S2Cl2 has been developed. This method is suitable for those cases when conventional procedures applying thionyl chloride do not work. The most pi-deficient compounds react with neutral carbon nucleophiles under mild conditions to give the corresponding 1,4-adducts to the pyridine ring.image

引用

页数：4

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