Synthesis of diverse β-(nitrooxy)-substituted amines by regioselective ring-opening of aziridines under neat conditions

Abstract

An efficient and regioselective method was developed for the synthesis of β-(nitrooxy)-substituted amine derivatives by ring-opening of different aziridines with Zn(NO₃)₂·6H₂O without using additives or catalyst. A library of β-(nitrooxy)-substituted amine derivatives having a variety of substituents has been synthesized. Excellent regioselectivity, high yields, clean reaction, ease of product isolation, easily accessible reactants, and solvent-free as well as environment friendly reaction conditions are the notable advantages of the present methodology. The nitrooxy derivative was successfully transformed into hydroxy derivative by simple reduction. Gram-scale synthesis demonstrates the potential applications of the present method.

Graphical Abstract

Keywords:

• β-Amino alcohol
• aziridines
• β-(nitrooxy)-substituted amines
• reduction
• regioselective

Additional information

Funding

A. Majee acknowledges the financial support from the DST-RSF Major Research Project [Ref. No. INT/RUS/RSF/P-08]. S. Santra and G. V. Zyryanov thank Russian Science Foundation [Ref. # 16-43-02020], by Act 211 Government of the Russian Federation [Ref. 02.A03.21.0006]. We are thankful to DST, Govt. of India and UGC-SAP.