Acid-Mediated Ring Expansion of 2,2-Disubstituted Azetidine Carbamates to 6,6-Disubstituted 1,3-Oxazinan-2-ones

被引：16

作者：

Boddy, Alexander J. ^{[1
]}

Cordier, Christopher J. ^{[1
]}

Goldberg, Kristin ^{[2
]}

Madin, Andrew ^{[3
]}

Spiyey, Alan C. ^{[1
]}

Bull, James A. ^{[1
]}

机构：

[1] Imperial Coll London, Dept Chem, Mol Sci Res Hub, White City Campus,Wood Lane, London W12 0BZ, England

[2] AstraZeneca, Med Chem Oncol, IMED Biotech Unit, Cambridge CB4 0WG, England

[3] AstraZeneca, Hit Discovery, Discovery Sci, IMED Biotech Unit, Cambridge CB4 0WG, England

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 06期

基金：

英国工程与自然科学研究理事会;

关键词：

STEREOCONTROLLED SYNTHESIS; SYNTHETIC APPLICATIONS; AZIRIDINES; REACTIVITY; OXAZOLIDIN-2-ONES; REGIOSELECTIVITY; AMINOPROPANES; PYRROLIDINES; HETEROCYCLES; INHIBITORS;

D O I：

10.1021/acs.orglett.9b00407

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ring expansion of 2-ester-2-arylazetidine carbamates can be achieved using Bronsted acids to form 6,6-disubstituted 1,3-oxazinan-2-ones. The reaction is rapid at room temperature with Boc or Cbz derivatives and proceeds with excellent yield (up to 96%) and broad substrate scope. Derivatives of drug compounds and natural products are incorporated. The combination of this ring expansion in a three-step N-H insertion/cyclization/expansion sequence is applied to directly access medicinally relevant scaffolds from acyclic precursors.

引用

页码：1818 / 1822

页数：5

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