Mild Intramolecular Ring Opening of Oxetanes

被引：19

作者：

DeRatt, Lindsey G. ^{[1
]}

Lawson, Edward C. ^{[1
]}

Wang, Chao-Yuan ^{[1
]}

Kuduk, Scott D. ^{[1
]}

机构：

[1] Janssen Res & Dev, 1400 McKean Rd, Spring House, PA 19477 USA

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 23期

关键词：

DRUG DISCOVERY; REACTIVITY; ENTHALPIES; EPOXIDES; ACCESS;

D O I：

10.1021/acs.orglett.9b03810

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxetanes have been increasingly used as stable motifs in medicinal chemistry as well as versatile synthetic intermediates. Herein, an intramolecular ring opening of oxetane carboxamides with mild nucleophiles, such as nitrogen heterocycles, is presented. The reaction proceeds under metal-free basic conditions which is highly unusual in ring opening reactions of oxetanes. Amide formation and oxetane ring opening/cyclization in a one-pot approach affords high levels of molecular complexity in a single step from simple, readily available substrates.

引用

页码：9642 / 9645

页数：4

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