Conversions of 2-(2-Oxo Cyclohexylcarbonyl)Benzoic Acid Derivatives to Pyrazolo[^[5], ^[1], ^[2], ^[3], ^[4], ^[5], ^[6], ^[7], ^[8], ^[9], ^[10]]Isoindole and Pyrimidine Rings

Abstract

Phtalic acid derivative of o-methylcarboxybenzoylchloride readily acylates N(1-cyclohexenyl) morpholine and is likely to acylate other enamines along the classic path to 1,3-diketones. It is a convenient route towards o-(1-(1,3-diketone)) derivatives of benzoic acid, which are precursors of o-(heteroaryl)-benzoic acids. Further conversions with hydrazines and amidines lead to pyrazolo[ ^[5] , ^[1] , ^[2] , ^[3] , ^[4] , ^[5] , ^[6] , ^[7] , ^[8] , ^[9] , ^[10] ]isoindole and pyrimidine rings respectively. The structures of the obtained compounds were confirmed by X-ray structure determinations.

Keywords:

• 1,3-Diketones
• enamines
• O-acylated enols
• pyrazolo[5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10]isoindoles
• pyrimidines
• X ray diffraction analysis

ACKNOWLEDGMENTS

This work was supported in the frame of a co-operation agreement between the Paul Sabatier University (Toulouse-France) and the Kiev National Taras Shevchenko University (Ukraine).