Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 12, Pages 8140-8150Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01014
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Funding
- MINECO [CTQ 2014-56887]
- Fundacion Seneca-CARM [19240/PI/14]
- Xunta de Galicia [ED418B 2016/166-0]
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C-Alkoxycarbonyl-C-phenyl-N-aryl ketenimines bearing 1,3-dithiolan-2-yl or 1,3-dithian-2-yl substituents at ortho position of the C-phenyl ring, respectively, transform into isoquino-line-1-thiones and quinolin-4-ones under thermal treatment in toluene solution. The formation of isoquinolinethiones involves a rare degradation of the 1,3-dithiolane ring, whereas, in contrast, the 1,3-dithiane ring remains intact during the reaction course leading to quinolin-4-ones. Computational density functional theory results support that the kinetically favorable mechanism for the formation of isoquinoline-l-thiones proceeds through a [1,5]-hydride shift/6 pi-electrocyclization cascade, followed by a thiirane extrusion process. Alternative mechanistic paths showing interesting electronic reorganization processes have been also scrutinized but resulted not competitive on energetic grounds.
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