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1,2,4‐Triazines. 8 . Reduction of 4‐methyl‐1,2,4‐triazin‐5(4 H )‐ones with sodium borohydride. Regioselective preparation of dihydro‐1,2,4‐triazin‐5(4 H )‐ones
Author(s) -
Sanemitsu Yuzuru,
Nakayama Yoshinori,
Mizutani Masato,
Oshie Kazuyuki
Publication year - 1984
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.5570210302
Subject(s) - chemistry , sodium borohydride , regioselectivity , borohydride , medicinal chemistry , sodium , organic chemistry , catalysis
Reduction of 3‐methylthio‐1,2,4‐triazin‐5(4 H )‐one ( 1a ) with sodium borohydride afforded 3‐methylthio‐1,6‐dihydrotriazin‐5(4 H )‐one ( 2b ) selectively. 3‐Methylthio‐6‐ t ‐butyl‐1,2,4‐triazin‐5(4 H )‐one ( 1d ) reacted with sodium borohydride to give mainly 6‐ t ‐butyl‐2,3‐dihydro‐1,2,4‐triazin‐5(4 H )‐one ( 3d ). The reaction of various 4‐methyl‐1,2,4‐triazin‐5(4 H )‐ones with sodium borohydride and the influence of bulkiness and electronic effect of the substituents at the 3‐ and 6‐positions upon the product ratio, are also discussed.