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Synthesis 2020; 52(19): 2857-2869
DOI: 10.1055/s-0040-1707405
paper
© Georg Thieme Verlag Stuttgart · New York

Synthetic Approach to Fused Azasultams with 1,2,4-Thiadiazepine Framework

Vasyl Y. Hys
a   Chemistry Department, Taras Shevchenko National University of Kyiv, Lva Tolstoho Street 12, Kyiv 01033, Ukraine   Email: milokhovds@gmail.com   Email: milokhovds@knu.ua
b   Enamine Ltd., Chervonotkatska Street 78, Kyiv 02660, Ukraine
,
Demyd S. Milokhov  ∗
a   Chemistry Department, Taras Shevchenko National University of Kyiv, Lva Tolstoho Street 12, Kyiv 01033, Ukraine   Email: milokhovds@gmail.com   Email: milokhovds@knu.ua
,
Olesya B. Volovenko
a   Chemistry Department, Taras Shevchenko National University of Kyiv, Lva Tolstoho Street 12, Kyiv 01033, Ukraine   Email: milokhovds@gmail.com   Email: milokhovds@knu.ua
b   Enamine Ltd., Chervonotkatska Street 78, Kyiv 02660, Ukraine
,
Irina S. Konovalova
c   Division of Functional Materials Chemistry, SSI ‘Institute for Single Crystals’, National Academy of Sciences of Ukraine, Nauky Avenue 60, Kharkiv 61001, Ukraine
,
Svitlana V. Shishkina
c   Division of Functional Materials Chemistry, SSI ‘Institute for Single Crystals’, National Academy of Sciences of Ukraine, Nauky Avenue 60, Kharkiv 61001, Ukraine
,
Yulian M. Volovenko
a   Chemistry Department, Taras Shevchenko National University of Kyiv, Lva Tolstoho Street 12, Kyiv 01033, Ukraine   Email: milokhovds@gmail.com   Email: milokhovds@knu.ua
› Author AffiliationsThe 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)

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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 chromatography

Supporting 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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