Synthesis of dihydro-2H-spiro [acenaphthylene-1,3′-pyrazole]: An approach toward apixaban moeity

Abstract

The 1,3-dipolar cycloaddition (DC) reaction of substituted acenaphthenone-2-ylidine ketone with nitrile imines to obtain the corresponding dihydro-2H-spiro [acenaphthylene-1,3′-pyrazole] cycloadducts in good to excellent yields (up to 92%) with regioselectivity. Nitrile imines were generated from hydrazonoyl chlorides in the presence of triethylamine as a base in dichloromethane solvent. The structure, and regiochemistry were determined by using spectroscopic data and confirmed by single-crystal X-ray diffraction analysis.

Graphical Abstract

Acknowledgments

One of the authors V. Nookaapparao Gorli thanks BIOCON limited, Bangalore, India and the director CSIR-Central Leather Research Institute, Adyar, Chennai 600 020, India for the research support.

Notes

1 CCDC-1905633 (3a) and CCDC-1905632 (3d) contains supplementary Crystallographic data for the structures. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre (CCDC), 12 Union Road, Cambridge CB2 1EZ, UK; fax: [phone]; email: [email protected]].