Synthesis of 3,4-Dihydro-2H,5H-pyrano[3,2-c][1]benzopyran-5-one Derivatives by Diels-Alder Reactions of 3-Methylenebenzopyran- 2,4-diones with Silyl Enol Ethers

Chin. J. Org. Chem. ›› 2009, Vol. 29 ›› Issue (05): 716-723. Previous Articles Next Articles

Original Articles

3-亚甲基苯并吡喃-2,4-二酮与烯醇硅醚的Diels-Alder反应合成3,4- 二氢-2H,5H-吡喃并[3,2-c][1]苯并吡喃-5-酮衍生物

彭大权^a,b ; 刘蕴^b ; 吕志锋^b; 徐建华^*,b

(a重庆师范大学化学学院重庆 400047)
(b南京大学化学化工学院南京 210093)

收稿日期:2007-09-16 修回日期:2008-10-20 发布日期:2009-05-20
通讯作者: 徐建华

Synthesis of 3,4-Dihydro-2H,5H-pyrano[3,2-c][1]benzopyran-5-one Derivatives by Diels-Alder Reactions of 3-Methylenebenzopyran- 2,4-diones with Silyl Enol Ethers

Peng, Daquan ^a,b ; Liu, Yun ^b; Lü, Zhifeng ^b; Xu, Jianhua^*,b

(a School of Chemistry, Chongqing Normal University, Chongqing 400047)
(b School of Chemistry & Chemical Engineering, Nanjing University, Nanjing 210093)

Received:2007-09-16 Revised:2008-10-20 Published:2009-05-20
Contact: Xu, Jianhua

Abstract

Quinone methides, generated in situ from the reaction of 4-hydroxycoumarin with benzaldehyde, formaldehyde and pentanal, underwent the Diels-Alder reaction with silyl enol ethers to give a series of 3,4-dihydro-2H,5H-pyrano[3,2-c][1]benzopyran derivatives in high yields. Steric configurations of five compounds were determined by X-ray diffraction experiments. The regioselectivity of the reactions was in-vestigated by frontier molecular orbital interactions between the reactants as calculated by a density func-tional theory (DFT) method, which well rationalized the observed data.

Key words: silyl enol ether, Diels-Alder reaction, pyrano[3,2-c][1]benzopyran, quinone methide

Cite this article

Peng, Daquan ^a,b ; Liu, Yun ^b; Lü, Zhifeng ^b; Xu, Jianhua^*,b. Synthesis of 3,4-Dihydro-2H,5H-pyrano[3,2-c][1]benzopyran-5-one Derivatives by Diels-Alder Reactions of 3-Methylenebenzopyran- 2,4-diones with Silyl Enol Ethers[J]. Chin. J. Org. Chem., 2009, 29(05): 716-723.

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3-亚甲基苯并吡喃-2,4-二酮与烯醇硅醚的Diels-Alder反应合成3,4- 二氢-2H,5H-吡喃并[3,2-c][1]苯并吡喃-5-酮衍生物

Synthesis of 3,4-Dihydro-2H,5H-pyrano[3,2-c][1]benzopyran-5-one Derivatives by Diels-Alder Reactions of 3-Methylenebenzopyran- 2,4-diones with Silyl Enol Ethers

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