H. Saikachi, H. Ogawa, Katutoshi Sato
Jan 25, 1971
Citations
0
Influential Citations
13
Citations
Journal
Chemical & Pharmaceutical Bulletin
Abstract
7, 8 : 17, 18-Dibenzo [20] annulene 1, 4 : 11, 14-dioxide all trans isomer (IV) has been synthesized from the Wittig reaction of di-trans 1, 2-bis [(β-5-formyl)-2-furyl]-vinyl benzene (IIIa) with o-xylene-bis-(triphenylphosphonium bromide) in fairly high yield (35%). The reaction of IIIa with o-phenylenediamine in tetrahydrofuran has been shown to yield three annelated products, i.e., 7, 8 : 17, 18-dibenzo-19, 20-dihydro-16, 19-diaza [20] annulene 1, 4 : 11, 14-dioxide (VI) in 15%, 16-H-7, 8 : 17, 18-dibenzo-15-keto-16, 19-diaza [20] annulene 1, 4 : 11, 14-dioxide (VII) in 1.0% and oxazirino [2, 3-s] 7, 8 : 17, 18-dibenzo-16-aza [20] annulene 1, 4 : 11, 14-dioxide (VIII) in 15.7% yield. The interrelationship among these products was discussed. The reaction of hydrazine hydrate and cis-α, β-di (5-formyl-2-furyl) ethylene (XIb) has been shown to yield dimeric [28] tetraazaannulene tetraoxide (XIII) in 2.5%, and no monomeric [14] diazaanulene dioxide (XII) or no other disproportionation products were obtained.