Author:
Shalimov Oleksandr,Rusanov Eduard,Muzychka Oksana,Onys’ko Petro
Abstract
A new effective method for the construction of nitrogen heterocycles incorporating endocyclic pharmacophore sulfonamide fragment, based on the use of easy accessible N-(chlorosulfonyl)imidoyl chloride, CCl3C(Cl)=NSO2Cl (1), has been developed. Thus, a reaction of 1 as bielectrophilic 1,3-C–N–S reagent with benzylamines that act as 1,4-N–C–C-C binucleophiles, affords respective 1,2,4-benzothiadiazepine-1,1-dioxides. On the other hand, 1 reacts with alkenyl amines with the formation of respective N-alkenyl amidines undergoing Lewis acids initiated intramolecular cyclization to afford derivatives of 1,2,4-thiadiazines and 1,2,4-thiadiazocines bearing a halomethyl group able for further functionalization. The first examples of electrophilic heterocyclization of the chlorosulfonyl group onto an alkenyl or alkynyl group have been revealed.
Subject
Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science
Reference38 articles.
1. Drug Discovery: A Historical Perspective
2. Facile Synthesis of 4H-1,2,4-Benzothiadiazine-1,1-dioxides
3. Correlation of antihypertensive activity with structure in a series of 2H-1,2,4-benzothiadiazine 1,1-dioxides using the substituent constant approach
4. 1,2,4-Benzothiadiazine derivatives as α1 and 5-HT1A receptor ligands
5. Antimicrobial action of 1,2,4-benzothiadiazine-1,1-dioxide derivatives;Dibella;Farmaco,1973
Cited by
4 articles.
订阅此论文施引文献
订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献
1. Expedient synthesis of 8-membered azasultams: A combined synthetic, DFT, and in vitro study;Tetrahedron Chem;2024-08
2. Efficient Synthesis of Fused Heterocycles Incorporating Pyrazole/Thiadiazine or Pyrazole/Thiadiazepine Fragments Using N‐Chlorosulfonyltrihaloacetimidoyl Chlorides;ChemistrySelect;2023-11-15
3. Novel convenient approach to 1,4,2-benzodithiazine-1,1-dioxides and 1,2,3-benzoxathiazine-2,2-dioxides;Arkivoc;2022-04-16
4. 1,2,4-Oxadiazines and 1,2,4-Thiadiazines;Comprehensive Heterocyclic Chemistry IV;2022