ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

An efficient synthesis of structurally diverse 2-methyl-N-[(3-phenylamino)oxetan-3-yl]-2-propanesulfinamide derivatives under catalyst free conditions

Sandip R. Ugale and Somnath S. Gholap

Padmashri Vikhe Patil College of Arts, Science and Commerce, District-Ahmednagar, India

E-mail: ssgholap2002@gmail.com

Abstract: A convenient and straightforward synthesis of structurally diverse 2-methyl-N-[(3-phenylamino)oxetan-3-yl]-2-propanesulfinamide derivatives from 3-oxetan-3-tert-butylsulfinimine and substituted aromatic amines in methanol at 60 °C temperature is described. The corresponding diaminooxetane derivatives are obtained in good to excellent yield under optimized reaction conditions. The method presented herein was found to be advantageous for diaminooxetane derivatives as emerging building block for future drug discovery. The title diaminooxetanes should be considered as bioisosteric to isopropylidenediamines and urea derivatives rather than to gem-dimethyl and carbonyl groups, respectively.

Keywords: 3-Oxetan-3-tert-butylsulfinimine; Amine; Diaminooxetane; Catalyst-free conditions

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-017-0237-1

Chemical Papers 71 (12) 2435–2443 (2017)