Iodine-catalyzed synthesis of fused tetracyclic pyridazino[6,1-b] pyrrolo[1,2-a]quinazolin-9(1H)-one derivatives via a tandem reaction

被引：15

作者：

Zhang, Wen-Ting ^{[1
]}

Qiang, Wen-Wen ^{[1
]}

Yao, Chang-Sheng ^{[1
]}

Wang, Xiang-Shan ^{[1
]}

机构：

[1] Jiangsu Normal Univ, Sch Chem & Chem Engn, Jiangsu Key Lab Green Synth Funct Mat, Xuzhou 221116, Jiangsu, Peoples R China

来源：

TETRAHEDRON | 2016年 / 72卷 / 17期

关键词：

Pyridazinopyrroloquinazoline; 2-Aminobenzohydrazide; Iodine; Tandem reaction; MOLECULAR-IODINE; QUINAZOLIN-4(3H)-ONES; EFFICIENT; QUINOLINES;

D O I：

10.1016/j.tet.2016.03.018

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile and general method for the synthesis of pyridazino[6,1-b]pyrrolo[1,2-a]quinazolin-9(1H)-one derivatives via a reaction of 2-aminobenzohydrazide and 1,7-dichloro-heptan-4-one catalyzed by iodine in the presence of excess NaHCO3 is described. This is a tandem reaction to construct three new rings and a chiral quaternary carbon center in one-pot procedure. Two possible pathways in the formation of the second heterocycle are proposed, and they are confirmed by the key intermediates of pyrrolo[1,2-a] quinazolin-5(1H)-ones which are selectively obtained via controlling the ratio of base. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：2178 / 2185

页数：8