53527-02-9

Upstream product

• 69141-45-3 5-isopropyl-2-tosyloxytropone 
• 100-63-0 phenylhydrazine 
• 672-76-4 gamma-thujaplicin 

Downstream Products

• 107752-61-4 2-Amino-5-(4-amino-phenyl)-4-isopropyl-cyclohepta-2,4,6-trienone 
• 121953-87-5 5-(4-acetamidophenyl)-4-isopropyltropolone 
• 121953-78-4 5-(4-acetamidophenyl)-4-isopropyltropolone acetate 
• 107752-73-8 5-(4-Amino-phenyl)-2-hydroxy-4-isopropyl-cyclohepta-2,4,6-trienone 

Relevant academic research and scientific papers

Synthesis and Reactions of 2-Arylhydrazinotropones. I. Preparation of 2-(2-Arylhydrazino)tropones and the 4-Substituted Derivatives

A wide variety of 2-(2-arylhydrazino)tropones were prepared by the reactions of 2-tosyloxytropone with arylhydrazines.The dimeric compounds 6,6'-bis(arylhydrazono)-1,1'-bi(2,4-cycloheptadiene)-7,7'-diones, 2-anilinotropones, and 3-(2-arylhydrazino)tropones were isolated as minor products in some cases.Similarly, starting with 2-tosyloxytropones bearing an isopropyl, isopropenyl, (1-acetamidoethyl), and protected acetyl group at the 5-position, 4-substituted 2-(2-arylhydrazino)tropones were obtained as the major products by the abnormal substitution reaction.These 2-(2-arylhydrazino)tropones are expected to effectively serve as precursor for a convenient synthesis of 5-aryl-substituted tropolones via benzidine-type rearrangement. 1H NMR (200 or 500-MHz) parameters for these 4-substituted 2-(2-arylhydrazino)tropones are given for their unambiguous structural assignments.

A Convenient Synthesis of 5-Aryltropolones via Novel Benzidine Type Rearrangement of 2-(2-Arylhydrazino)tropones

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, i.e. 2-amino-5-(4-aminoaryl)tropones, which in turn were conveniently led to the corresponding 5-aryltropolones that can be utilized for synthesizing B-ring-open analogues of colchicine.