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5‐Amino‐4,5‐dihydroisoxazoles. Part I. 5‐Amino‐3‐aryl‐4‐methylene‐4,5‐dihydroisoxazoles and 4‐aminomethyl‐3‐arylisoxazoles from 5‐amino‐4‐aminomethyl‐3‐aryl‐4,5‐dihydroisoxazoles
Author(s) -
Pocar Donato,
Rossi Luisa Maria,
Trimarco Pasqualina,
Vago Luciano
Publication year - 1980
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570170508
Subject(s) - chemistry , aryl , deamination , methylene , nitrile , catalysis , yield (engineering) , cycloaddition , organic chemistry , iodide , medicinal chemistry , alkyl , materials science , metallurgy , enzyme
5‐Amino‐4‐aminomethyl‐3‐aryl‐4,5‐dihydroisoxazoles 2 were obtained by cycloaddition of nitrile oxides to 1,3‐diaminopropenes 1. On reaction with methyl iodide the corresponding 4‐(quaternary)‐ammoniomethyl iodides 3 were formed. These compounds, on reaction with bases, afforded 5‐amino‐3‐aryl‐4‐methylene‐4,5‐dihydroisoxazoles 4. The acid‐catalyzed deamination of compounds 2 afforded 4‐aminomethyl‐3‐arylisoxa‐zoles 5 and 3‐arylisoxazoles as retro‐Mannich products. The deamination of 2 to yield 5 was also obtained by base catalysis.