Synthesis of 1H-quinazoline-4-ones using intramolecular aromatic nucleophilic substitution

被引：10

作者：

Bowman, WR ^{[1
]}

Heaney, H ^{[1
]}

Smith, PHG ^{[1
]}

机构：

[1] Loughborough Univ Technol, Dept Chem, Loughborough LE11 3TU, Leics, England

来源：

ARKIVOC | 2003年

关键词：

intramolecular SNAr; intramolecular S(RN)1; 2-thioxo-2,3-dihydro-1H-quinazolin-4-ones; 1H-quinazoline-2,4-diones; Cu(I)-catalyzed rearrangement;

D O I：

10.3998/ark.5550190.0004.a41

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The anions of 1-(2-bromobenzoyl)-3-phenylthiourea 1, 1-(2-chlorobenzoyl)-3-phenylthiourea 2 and 1-(2-bromobenzoyl)-3-phenylurea 8 undergo intramolecular nucleophilic substitution (putative SNAr mechanism), and not intramolecular S(RN)1 substitution, to yield 1-phenyl-2-thioxo-2,3-dihydro-1H-quinazolin-4-one 6 and 1-phenyl-1H-quinazoline-2,4-dione 9 respectively. Under the same reaction conditions with the addition of copper(I) iodide, phenylthioureas 1 and 2 gave a rearrangement to the respective 2-halogeno-N-phenyl-benzamides.

引用

页码：434 / 442

页数：9

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