Synthesis of 2-aryl-1,2,3,4-tetrahydroquinazolin-1-ols and their conversion to 7-aryl-9H-6-oxa-5,8-diaza-benzocycloheptenes

被引：22

作者：

Coskun, N ^{[1
]}

Çetin, M ^{[1
]}

机构：

[1] Uludag Univ, Dept Chem, TR-16059 Bursa, Turkey

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 49期

关键词：

quinazoline; quinazolin-1-ol; 6-oxa-5,8-diaza-benzocycloheptenes; benzo[c]oxadiazepine; ring expansion; oxidation with H(2)O(2-)tungstate; rearrangement;

D O I：

10.1016/j.tetlet.2004.10.062

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Aminobenzylamine was reacted with corresponding aromatic or heteroaromatic aldehydes to give 1,2,3,4-tetrahydroquinazolines 1 the oxidation of which with H2O2-tungstate in methanol led to the formation of the corresponding 1,2,3,4-tetrahydroquinazolin-1-ols 2. A one-pot procedure involving the treatment of the in situ formed quinazoline 1 with H2O-tungstate again led to the formation of 2. Compounds 2 react with 2equiv of aryl isocyanate in toluene at room temperature to produce compounds 3. The probable mechanism of the ring-expanding carbamoylation of quinazolin-1-ols 2 to 6-oxa-5,8-diaza-benzocycloheptenes 3 is discussed. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：8973 / 8975

页数：3

共 11 条

[1] Erlotinib: a new therapeutic approach for non-small cell lung cancer [J].