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Synthesis of 3‐aminoalkyl‐2‐arylaminoquiazolin‐4(3 H )‐ones and 3,3′‐disubstituted bis‐2‐arylaminoquinazolin‐4(3 H )‐ones via reactions of 1‐aryl‐3‐(2‐ethoxycarbonylphenyl)carbodiimides with diamines
Author(s) -
Yang XuHong,
Wu MingHu,
Sun ShaoFa,
Xie JiaLi,
Ding MingWu,
Xia QingHua
Publication year - 2008
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.5570450518
Subject(s) - chemistry , regioselectivity , wittig reaction , aryl , structural isomer , molar ratio , medicinal chemistry , stereochemistry , organic chemistry , catalysis , alkyl
1‐Aryl‐3‐(2‐ethoxycarbonylphenyl)carbodiimides 2 , obtained from aza‐Wittig reactions of iminophosphorane 1 with aryl isocyanates, reacted with primary diamines in 1:1 and 2:1 molar ratio under mild conditions to give selectively the regioisomers 3‐aminoalkyl‐2‐arylaminoquinazolin‐4(3 H )‐ones 3 and 3,3′‐disubstituted bis‐2‐arylaminoquinazolin‐4(3 H )‐ones 4 in good yields, respectively. To fully characterize the regioselectivity of aza‐Wittig reactions of 1‐aryl‐3‐(2‐ethoxycarbonylphenyl)carbo‐diimides with primary diamines, crystals of 4e were obtained, and its structure was determined by X‐ray crystallography.