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Synthesis of Isoxazoline Derivatives Based on Nitrile Oxide Cycloaddition of Nitroso‐Nitro‐Enamine
Author(s) -
Kondacs László András,
Pilipecz Mihály Viktor,
Mucsi Zoltán,
Balázs Barbara,
Gáti Tamás,
Nyerges Miklós,
Dancsó András,
Nemes Péter
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500905
Subject(s) - chemistry , enamine , nitrile , nitroso , cycloaddition , moiety , 1,3 dipolar cycloaddition , nitro , oxime , pyrroline , reagent , nitroso compounds , nitrone , medicinal chemistry , organic chemistry , stereochemistry , catalysis , alkyl
A new and stable nitroso‐nitro‐enamine reagent, providing a nitrile oxide 1,3‐dipole, has been treated with dipolarophiles in the course of 1,3‐dipolar cycloaddition reactions to give a large number of novel isoxazolyl‐pyrroline derivatives. Surprisingly, instead of the expected 2‐isoxazolyl‐dihydropyrrole cycloadducts, dihydropyrrol‐3‐one oximes were isolated as the main products in most cases. The imino‐oxime moiety was successfully transformed into 3‐aminopyrrole derivatives. The mechanism and selectivity of the reactions were also studied by experimental and theoretical methods [WB97XD/6‐311++G(2d,2p)//B3LYP/6‐311++G(2d,2p)], including the solvent effect.