N-Morpholinomethyl-5-Iithiotetrazole: A Reagent for the One-Pot Synthesis of 5-(1-Hydroxyalkyl)tetrazoles

被引：9

作者：

Alexakos, Panagiotis D. ^{[1
]}

Wardrop, Duncan J. ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, 845 West Taylor St, Chicago, IL 60607 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 19期

关键词：

TETRAZOLE CHEMISTRY; MEDICINAL CHEMISTRY; FRAGMENTATION; CARBANIONS; LITHIATION; INHIBITORS; TRIAZOLES; CARBENES; LIGANDS; 5-ARYL;

D O I：

10.1021/acs.joc.9b01885

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient, one-pot method for the preparation of 5-(1-hydroxyalkyl)tetrazoles is reported. N-Morpholinomethyl-5-lithiotetrazole, generated by the deprotonation of 4-(N-tetrazolylmethyl)morpholine with LiHMDS, undergoes addition to ketones and aldehydes (both aromatic and aliphatic) to form 5-(1-hydroxyalkyl)-tetrazoles in a high yield, after acidic workup. The reported protocol displays a broad substrate scope and functional group tolerance, avoids the use of cyanide- or azide-based reagents, and provides access to sterically congested and unsaturated tetrazoles, which are difficult to access by other means.

引用

页码：12430 / 12436

页数：7

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