Synthesis of complex fused polycyclic heterocycles utilizing IMDAF reactions of allylamino- or allyloxy-furyl(hetero)arenes

被引：20

作者：

Read, Matthew L.

Krapp, Andreas ^{[1
]}

Miranda, Pedro O.

Gundersen, Lise-Lotte ^{[1
]}

机构：

[1] Univ Oslo, Dept Chem, Ctr Theoret & Computat Chem, N-0315 Oslo, Norway

来源：

TETRAHEDRON | 2012年 / 68卷 / 07期

关键词：

Heterocycles; IMDAF reactions; Polycyclic compounds; Stereoselectivity; BASIS-SETS; CORE; CONSTRUCTION; DERIVATIVES; ANALOGS; RI-MP2; RN;

D O I：

10.1016/j.tet.2011.12.079

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Arenes and heteroarenes carrying a halogen and an amino- or hydroxy group have been converted to allylamino- or allyloxy-furyl-(hetero)arenes. These compounds underwent IMDAF reactions to give complex fused polycyclic heterocycles. The reactivity of the substrates was highly dependent on the detailed substitution pattern, however cyclizations occurred with high stereoselectivity in most cases. Experimental findings regarding reactivity and stereoselectivity were supported by calculations. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：1869 / 1885

页数：17