"All-Aqueous" Tandem Boc-Deprotection and Alkylation of N-Bocbenzimidazole Derivatives under Visible Light with Alkyl Aryl Diazoacetates: Application to Site-Selective Insertion of Carbenes into the N-H Bond of Purines

被引：2

作者：

Rath, Suchismita ^{[1
]}

Mohanty, Biswajit ^{[1
]}

Sen, Subhabrata ^{[1
]}

机构：

[1] Shiv Nadar Inst Eminence Deemed Univ, Sch Nat Sci, Dept Chem, Dadri 201314, Uttar Pradesh, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 02期

关键词：

ACYCLIC NUCLEOSIDE PHOSPHONATES; 1,2-DISUBSTITUTED BENZIMIDAZOLES; MECHANISTIC INSIGHT; PROTECTING GROUP; ROUTE; HETEROCYCLES; ACTIVATION; EFFICIENT; REMOVAL; INDOLES;

D O I：

10.1021/acs.joc.2c02467

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we have reported a blue LED-induced tandem Boc-deprotection and NH-alkylation of benzimidazole derivatives with methyl aryl diazoacetates. The reactions occur in water at room temperature. The desired products are obtained in good to excellent yields. The putative mechanism of this reaction is discussed based on control experiments and supported by DFT studies. Additionally, the strategy is used to alkylate various purine derivatives via site-selective N1-alkylation to generate acyclic nucleoside analogues.

引用

页码：1036 / 1048

页数：13