74417-34-8Relevant academic research and scientific papers
Heterocyclic Quinonoid Chromophoric Systems : Part V - Synthesis of 3,4-Phthaloyl-2-thiaquinolizine
Shah, J. N.,Tilak, B. D.
, p. 29 - 36 (2007/10/02)
Condensation of α-mercaptomethylpyridine with 1,4-naphthoquinone, 2-chloro-1,4-naphthoquinone and 2,3-dichloro-1,4-naphthoquinone leads to a number of quinonoid derivatives including the desired 2-α-pyridylmethylmercapto-1,4-naphthoquinone (XVI) and its 3-chloro derivative (XI).Cyclization of XVI and XI gives 3,4-phthaloyl-2-thiaquinolizine (I) which represents a new heterocyclic quinonoid chromophoric system.Plausible mechanisms for the formation of the different heterocyclic quinones are discussed.Interaction of 1,4-naphthoquinone with 1-mercaptomethylisoquinoline affords 8,9-benzo-3,4-phthaloyl-2-thiaquinolizine (XXI).The thiaquinolizines undergo sulphur extrusion on heating to m.p. or on treatment with alkaline dithionite to yield the corresponding 2,3-phthaloylpyrrocolines.
