TY - JOUR

T1 - Calcium-mediated one-pot preparation of isoxazoles with deuterium incorporation

AU - Ledovskaya, Maria S.

AU - Rodygin, Konstantin S.

AU - Ananikov, Valentine P.

N1 - Funding Information: We gratefully acknowledge the financial support from the Russian Science Foundation (Project No 16-13-10301). This research made use of resources from the X-ray Diffraction Centre, Centre for Magnetic Resonance, Educational Resource Center of Chemistry and the Centre for Chemical Analysis and Materials of Saint-Petersburg State University. Publisher Copyright: © 2018 the Partner Organisations. Copyright: Copyright 2018 Elsevier B.V., All rights reserved.

PY - 2018/1/21

Y1 - 2018/1/21

N2 - In this work, a novel synthetic methodology for the one-pot preparation of isoxazoles directly from the reaction of calcium carbide with aldoximes is reported. Calcium carbide acts as a safe and inexpensive acetylene source and, in addition, as a source of the Ca(OH)2 base to enable the generation of nitrile oxide. Various 3-substituted isoxazoles were synthesized from the corresponding aldoximes in good yields (up to 95%) and a series of new deuterated 4,5-dideuteroisoxazoles were prepared.

AB - In this work, a novel synthetic methodology for the one-pot preparation of isoxazoles directly from the reaction of calcium carbide with aldoximes is reported. Calcium carbide acts as a safe and inexpensive acetylene source and, in addition, as a source of the Ca(OH)2 base to enable the generation of nitrile oxide. Various 3-substituted isoxazoles were synthesized from the corresponding aldoximes in good yields (up to 95%) and a series of new deuterated 4,5-dideuteroisoxazoles were prepared.

UR - http://www.scopus.com/inward/record.url?scp=85040918986&partnerID=8YFLogxK

U2 - 10.1039/c7qo00705a

DO - 10.1039/c7qo00705a

M3 - Article

AN - SCOPUS:85040918986

VL - 5

SP - 226

EP - 231

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

SN - 2052-4110

IS - 2

ER -