Chalcogenation/pyrrolo(pyrido)annulation of 2-(3-butenyl)quinazolin-4(3H)-ones by arylsulfenyl(selenyl) chlorides. (9th April 2022)

• Record Type: Journal Article
• Authors: Vaskevych, Alla I.; Savinchuk, Nataliia O.; Vaskevych, Ruslan I.; Rusanov, Eduard B.; Vovk, Mykhailo V.
• Is Part Of: Tetrahedron. Volume 111(2022)
• Publication Date: 2022-04-09
• Subjects: 2-Butenyl quinazolinones -- Chalcogenation -- Annulation -- pyrrolo(pyrido)quinazolinones; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2022.132722
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Arylsulfenyl chlorides react with 2-(3-butenyl)quinazolinones in dichloromethane by the AdE addition mechanism to give 2-(3-arylthio-4-chlorobutyl)quinazolin-4 (3 Н )-ones, which, when heated in the presence of sodium acetate, cyclize to 8-arylthio-6, 7, 8, 9-tetrahydropyrido [2, 1- b ]quinazolin-11-ones. Arylsulfenylation (selenylation) of 2-(3-butenyl)quinazolinones conducted in nitromethane in the presence of an equimolar amount of lithium perchlorate proceeds as an electrophilic 5- exo-trig cyclization involving either of the nitrogen atoms of the quinazolone nucleus to yield 1-arylthio (selenyl)methyl substituted angular-annulated 2, 3-dihydropyrrolo [1, 2- a ]quinazolin-5(1 H )-ones as major products and isomeric linear-annulated 2, 3-dihydropyrrolo [2, 1- b ]quinazolin-9(1 H )-one derivatives as minor products. Graphical abstract: Image 1