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Synthesis 2020; 52(19): 2857-2869
DOI: 10.1055/s-0040-1707405
DOI: 10.1055/s-0040-1707405
paper
Synthetic Approach to Fused Azasultams with 1,2,4-Thiadiazepine Framework
The work was funded by Ministry of Education and Science of Ukraine (Grant No. 19BF037-03) and Enamine Ltd.Further Information
Publication History
Received: 28 March 2020
Accepted after revision: 18 May 2020
Publication Date:
16 June 2020 (online)
Abstract
Synthetic approach to fused azasultams with 1,2,4-thiadiazepine framework via base promoted protocols has been developed. 1H-Azole-2-carboxylates and N-(chloromethyl)-N-methylmethanesulfonamide were used as ambiphilic building blocks in the one-pot and two-step reaction sequences. Chemical behavior of the obtained azasultams in reactions with amines, hydrazine, DMFDMA, and NaBH4 was investigated. An enamino ketone derived from an azasultam was exploited in the synthesis of new pyrazole and pyrimidine heterocycles.
Key words
sulfonamides - sultams - thiadiazepine - pyrrole-2-carboxylate - indole-2-carboxylate - cyclization - sulfa-Dieckmann condensation - supercritical fluid chromatographySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707405.
- Supporting Information
Primary Data
- for this article are available online at https://doi.org/10.1055/s-0040-1707405 and can be cited using the following DOI: 10.4125/pd0118th.
- Primary Data
-
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