Bulletin of the Chemical Society of Japan p. 128 - 142 (1989)
Update date:2022-08-05
Topics:
Nozoe, Tetsuo
Takase, Kahei
Yasunami, Masafumi
Ando, Masayoshi
Saito, Hiroaki
et al.
Treatment of a wide variety of 2-(2-arylhydrazino)tropones with ethanolic acid at 50-80 deg C readily gave the benzidine type rearrangement products, 2-amino-5-(4-aminoaryl)tropones, besides minor amounts of byproducts of various type.The main products were conveniently led to the corresponding 5-aryltropolones.Similarly, 2-(2-arylhydrazino)tropones bearing an isopropyl and isopropenyl group at the 4-position afforded 4-substituted 2-amino-5-(4-aminoaryl)tropones as the main products, which were also led to 4-substituted 5-(4-acetamidoaryl)- and 5-(4-methoxyaryl)tropolones.Structural assignments of these products were made on the basis of 1H NMR and other spectral data as well as of chemical transformations to known 5-phenyltropolone and also to 2-acetamido-8-hydroxy-10,10-dimethylcycloheptinden-7(10H)-one.This synthetic scheme may possibly be utilized for a convenient synthesis of B-ring-open analogues of colchicine.
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