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Synthesis of 3-aminoalkyl-2-arylaminoquiazolin-4(3H)-ones and 3,3′-disubstituted bis-2-arylaminoquinazolin-4(3H)-ones via reactions of 1-aryl-3-(2-ethoxycarbonylphenyl)carbodiimides with diamines

✍ Scribed by Xu-Hong Yang; Ming-Hu Wu; Shao-Fa Sun; Jia-Li Xie; Ming-Wu Ding; Qing-Hua Xia

Publisher
Journal of Heterocyclic Chemistry
Year
2008
Tongue
English
Weight
411 KB
Volume
45
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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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.

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## Abstract The reaction of methyl anthranilate with 4,5‐dichloro‐1,2,3‐dithiazolium chloride (Appel's salt) in the presence of pyridine (2 equivalents) in dichloromethane at room temperature gave methyl __N__‐(4‐chloro‐5__H__‐1,2,3‐dithiazol‐5‐ylidene)anthranilate (3a) (50% yield), which reacted w