Pyrrolo[2,3-d]pyrimidine synthesis through activation of N-benzyl groups by distal amides

被引：15
作者：
El Kaim, Laurent [1 ]
Grimaud, Laurence [2 ]
Wagschal, Simon [1 ]
机构：
[1] Ecole Polytech, ENSTA, CNRS, Paristech,Lab Chim & Procedes,UMR 7652, F-91120 Palaiseau, France
[2] Ecole Normale Super, Lab Electrochim, Dept Chim, UMR CNRS ENS UPMC 8640, F-75231 Paris 05, France
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2013年 / 11卷 / 40期
关键词：
SMILES; ISOCYANIDES; DERIVATIVES; COUPLINGS; ARYLATION; ACCESS;
D O I：
10.1039/c3ob41477a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new activation mode of CH2-benzylamino groups has been observed during the preparation of pyrrolopyrimidines from Ugi-Smiles adducts of hydroxypyrimidines. The cyclization proceeds via a formal deprotonation of the N-benzyl group followed by trapping of the resulting anion by the alkyne moiety. The key role of the vicinal amide function during the process was pointed out.
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收藏
页码：6883 / 6885
页数：3
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