Tetrahedron Letters p. 5637 - 5640 (1995)
Update date:2022-07-29
Topics:
Laskos
Lianis
Rodios
Terzis
Raptopoulou
1-(N,N-diaroyl)amino-4-phenyl-1,2,3-triazol-5-yl-methyltriphenylphosph onium bromide 2 reacted with potassium t-butoxide or triethylamine in dry toluene giving the very stable phosphorus ylide 5. Refluxing of 5 in xylene gave the unexpected 3-aroyl-6-aryl-pyrazolo[4,3-d][2,3]benzodiazepines 6 by a Dimroth-like rearrangement of the triazole ring and a 1,7-electrocyclization of the nitrilimine intermediate 11. When the xylene solution was not rigorously refluxed the 3(5)-aroyl-5(3)-phenyl pyrazole 7 was isolated. The x-ray crystal structures of compounds 5d and 6b are also given.
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Doi:10.1039/c39950002275
(1995)Doi:10.1007/BF00475534
()Doi:10.1039/jr9380000545
(1938)Doi:10.1039/b602536f
(2006)Doi:10.1055/s-1995-4037
(1995)Doi:10.1021/om000223y
(2000)