Reactions of Azines. 12. Preparation and Reactions of Triphenylphosphonium Bromide

Article abstract of DOI:10.1021/jo00385a029

Preparation of triphenyl<2-((phenyl(methoxycarbonyl)methylene)hydrazono)propyl>phosphonium bromide (13), triphenyl<1-methyl-2-((phenyl(methoxycarbonyl)methylene)hydrazono)propyl>phosphonium iodide (15), and their corresponding ylides 14 and 16 was accomplished.The reaction of 14 with diphenylketene gave 2-methyl-4,9-diphenyl-9-(methoxycarbonyl)-4,9-dihydropyrazolo<1,5-b>isoquinoline (19/20).The reaction of 16 with phenyl isocyanate gave 6,7-dimethyl-3-methoxy-1,3-diphenyl-1H-imidazo<1,2-b>pyrazol-2(3H)-one (27b), 2,3-dimethyl-9-(methoxycarbonyl)-9-phenyl-4,9-dihydropyrazolo<5,1-b>quinazoline (30), and 2,3-dimethyl-9-phenylpyrazolo<5,1-b>quinazoline (31).Phenylacetoxyketene, on reacting with triphenyl<2-((diphenylmethylene)hydrazono)propyl>phosphorane (35), gave 2-methyl-4,9-diphenylpyrazolo<1,5-b>isoquinoline (40).Carbon disulfide with ylide 16 gave the 2,3-dimethyl-9-(methoxycarbonyl)-9H-pyrazolo<5,1-b><1,3>benzothiazine (45) and desaurine (42) as well as the trans-5,10-bis(methoxycarbonyl)-5,10-diphenyldipyrazolo<1,5-a:1',5'-e><1,5>diaza<3,6>dithiocine (46).Confirmation of the structures 31, 42, and 46 was obtained by crystallographic analyses.