Reactions of Cyanothioformamide and Thiohydantoin Derivatives With Some Arylidenes of Cyanothioacetamide and Other Elecetrophilic and Nucleophilic Reagents

Abstract

N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)cyanothioformamide was synthesized from the corresponding 4-amino-pyrazole. Various cyanothioformamides were reacted with different arylidenes of cyanothioacetamide to produce either 4-imino-5-thioxo-3-(pyrroline & pyrrolidine)carbonitrile or pyrrolo[3,2-d]thiazole. Interaction of thiohydantoin with the arylidenes of either malononitrile or cyanothioacetamide furnished the same 5-aminothiopyrano[2,3-d]-imidazole-6-carbonitriles. Also, thiohydantoin reacted with the anilide of chloroacetic acid and with anthranilic acid to produce thieno[2,3-d]-imidazole-2-one and imidazo[4,5-b]quinoline-2,9-dione, respectively.

Acknowledgments

Many thanks for Prof. Dr. E. Schaumann, Institüt fur Organische Chemie, Technische Universitat Claushthal, Leibnizstra Be 6 for his great help in making ¹HNMR and ¹³CNMR.

Many thanks for Prof. Dr. Roger Katcham, Prof. of Chem. and Pharm. Chem. Dept. of Pharm. Chem. School of pharmacy, Univ. of California, San Francisco, CA 94143-0446, USA. I began the work in this field at his lab. under his supervision since 1981, when I was a visiting Professor there.