96207-50-0Relevant academic research and scientific papers
Reactions of 9-Substituted 9-Thia-10-azaphenanthrenes with Electrophiles
Shimizu, Hiroshi,Ozawa, Michinori,Matsuda, Takayuki,Ikedo, Koji,Kataoka, Tadashi,et al.
, p. 1709 - 1718 (2007/10/02)
Reactions of 9-substituted 9-thia-10-azaphenanthrenes with several electrophiles have been investigated.Reaction of 9-alkyl-9-thia-10-azaphenanthrenes with dimethyl acetylenedicarboxylate (DMAD) afforded dibenzothiazonine derivatives 4 and 5, dibenzothiazocine derivatives 6, 2-alkylsulfinyl-2'-vinylaminobiphenyls 7, and bis(phenylylimino)ethane derivatives 8.The product distribution was markedly influenced by the substituent on the sulfur atom. 9-Methyl 3a and 9-isopropyl derivatives 3d afforded predominantly dibenzothiazonine derivatives 5a and 4d, respectively, while 9-ethyl 3b, 9-isopropyl 3c and 9-cyclohexyl derivatives 3e gave predominantly dibenzothiazocine derivatives 6 and alkylsulfinyl vinylaminobiphenyls 7.In contrast, the reactions of 9-phenyl 3f or 9-vinyl-9-thia-10-azaphenanthrene 3g with DMAD afforded only the corresponding dibenzothiazocine derivative 6.Reactions of 9-alkylthiaazaphenathrenes 3a-c with methyl propiolate (MP) in benzene afforded dibenzothiazecine derivatives 12 as 1:2 adducts.Reactions of compounds 3a-c with diphenylcyclopropenone in ethanol yielded the ring-opened product 13, while the same reaction in benzene solvent afforded the 4-quinolone derivative 14 via intramolecular cyclization of a ketene intermediate, L.
