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Preparation of N ‐aryl‐2,4‐diaminopentanes by the ring opening reaction of 1‐aryl‐3,4,5,6‐tetrahydro‐2‐(1 H )pyrimidinones
Author(s) -
Kashima Choji,
Katoh Akira,
Yoshiwara Nobutoshi,
Omote Yoshimori
Publication year - 1981
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.5570180821
Subject(s) - chemistry , pyrimidinones , aryl , yield (engineering) , ring (chemistry) , aluminum hydride , medicinal chemistry , lithium (medication) , organic chemistry , ion , medicine , alkyl , materials science , metallurgy , endocrinology , methoxide
1‐Aryl‐3,4,5,6‐tetrahydro‐2‐(1 H )pyrimidinones (I) underwent reductive ring opening reaction with lithium aluminum hydride to afford N ‐aryl‐2,4‐diaminopentanes (II) in good yields. On the other hand, 3,4,5,6‐tetrahydro‐3,4,6‐trimethyl‐1‐phenyl‐2‐(1 H )‐pyrimidinone (V) gave only cyclic diamine, 3,4,6‐trimethyl‐1‐phenylhexahydropyrimidine (VI), in 60% yield.