Journal
TETRAHEDRON LETTERS
Volume 60, Issue 6, Pages 475-479Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2019.01.001
Keywords
Di(2-pyridinyl) disulfide; Di(2-pyridinyl) diselenide; 2-Pyridinesulfenyl halides; 2-Pyridineselenenyl halides; Thiazolo[3,2-a]pyridin-4-ium derivatives; Selenazolo[3,2-a]pyridin-4-ium derivative
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Funding
- Russian Science Foundation [18-13-00372]
- Russian Science Foundation [18-13-00372] Funding Source: Russian Science Foundation
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Regioselective synthesis of a novel family of water-soluble 2H,3H-[1,3]chalcogenazolo[3,2-a]pyridin4-ium derivatives was developed based on 2-pyridinesulfenyl and -selenenyl halides and unsaturated compounds. The annulation reactions with divinyl sulfide, selenide and N-vinylpyrrolidin-2-one led to addition of the chalcogen atom to the terminal carbon of the double bond whereas the reaction with tetravinylsilane proceeded with opposite regiochemistry. Tricyclic condensed heterocycles were obtained from 2,3-dihydrofuran and cycloalkenes. The products represent novel promising scaffolds for organic synthesis and possible drug discovery. (C) 2019 Elsevier Ltd. All rights reserved.
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