Knoevenagel condensation of cyclic ketones with benzoylacetonitrile and N,N′-dimethylbarbituric acid. Application of sterically hindered condensation products in the synthesis of spiro and dispiropyrans by hetero-Diels-Alder reactions

被引：23

作者：

Palasz, Aleksandra ^{[1
]}

Palasz, Tadeusz ^{[2
]}

机构：

[1] Jagiellonian Univ, Dept Organ Chem, PL-30060 Krakow, Poland

[2] Jagiellonian Univ, Marian Smoluchowski Inst Phys, PL-30059 Krakow, Poland

来源：

TETRAHEDRON | 2011年 / 67卷 / 07期

关键词：

Spiro compounds; Hetero-Diels-Alder reactions; 1-Oxa-1,3-butadienes; Uracils; ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; ONE-POT SYNTHESIS; ENOL ETHERS; DERIVATIVES; 3,4-DIHYDRO-2H-PYRANS; CHEMISTRY; CYANIDES; WATER; ACYL;

D O I：

10.1016/j.tet.2010.12.053

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Inverse-electron demand Diels-Alder cycloadditions of sterically hindered cycloalkylidene derivatives of benzoylacetonitrile and N,N'-dimethylbarbituric acid with enol ethers, cyclic enol ethers and also sterically hindered cycloalkylidenecycloalkanes were investigated. New spiro, dispirodihydropyrans, spirouracils, and dispirouracils were obtained. To confirm the experimental results, frontier orbital HOMO and LUMO energies of heterodienes and dienophiles were calculated by semi-empirical AM1, PM3 methods and ab initio Hartree Fock calculations. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：1422 / 1431

页数：10