1,6-Addition Arylation of para-Quinone Methides: An Approach to Unsymmetrical Triarylmethanes

被引：93
作者：
Gao, Shang [1 ,2 ]
Xu, Xiuyan [1 ,2 ]
Yuan, Zhenbo [1 ,2 ]
Zhou, Haipin [1 ,2 ]
Yao, Hequan [1 ,2 ]
Lin, Aijun [1 ,2 ]
机构：
[1] China Pharmaceut Univ, Sch Pharm, SKLNM, Nanjing 210009, Jiangsu, Peoples R China
[2] China Pharmaceut Univ, Sch Pharm, Dept Med Chem, Nanjing 210009, Jiangsu, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 17期
基金：
中国国家自然科学基金;
关键词：
Synthetic methods; Polycycles; Carbocycles; Triarylmethanes; ASYMMETRIC 1,6-CONJUGATE ADDITION; CATALYZED CROSS-COUPLINGS; ALPHA-ISOCYANOACETAMIDES; AROMATIC-ALDEHYDES; EXPEDIENT ACCESS; DERIVATIVES; ACID; OXAZOLES; ARYL; DIARYLMETHANES;
D O I：
10.1002/ejoc.201600385
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A 1,6-addition arylation reaction of para-quinone methides with alpha-isocyanoacetamides and electron-rich aromatic compounds under metal-free conditions has been developed. BF3 center dot Et2O plays two roles in the reaction: catalyzing the cyclization of alpha-isocyanoacetamides to give oxazoles, and activating the para-quinone methides to achieve the 1,6-addition arylation process. The reaction shows good functional group tolerance, scalability, and regioselectivity. It is a consice protocol for the synthesis of diverse unsymmetrical triarylmethanes. Further transformation of the resulting triarylmethanes provides an efficient route to some functionalized molecules.
引用
收藏
页码：3006 / 3012
页数：7
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