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

被引：18

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

共 64 条

[11] Highly stereoselective ring expansion of enantiopure α-hydroxyalkyl azetidines [J].

Couty, F ;

Durrat, F ;

Prim, D .

TETRAHEDRON LETTERS, 2003, 44 (28) :5209-5212

[12] Ring expansions of 2-alkenylazetidinium salts - a new route to pyrrolidines and azepanes [J].

Couty, Francois ;

Durrat, Francois ;

Evano, Gwilherm ;

Marrot, Jerome .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (18) :4214-4223

[13] 2-Cyanoazetidines and Azetidinium Ions: Scaffolds for Molecular Diversity [J].

Couty, Francois ;

Drouillat, Bruno ;

Evano, Gwilherm ;

David, Olivier .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (11) :2045-2056

[14] Azetidines: New Tools for the Synthesis of Nitrogen Heterocycles [J].

Couty, Francois ;

Evano, Gwilherm .

SYNLETT, 2009, (19) :3053-3064

[15] Assessing the Rates of Ring-Opening of Aziridinium and Azetidinium Ions: A Dramatic Ring Size Effect [J].

De Rycke, Nicolas ;

David, Olivier ;

Couty, Francois .

ORGANIC LETTERS, 2011, 13 (07) :1836-1839

[16] Bicyclic Aziridinium Ions in Azaheterocyclic Chemistry - Preparation and Synthetic Application of 1-Azoniabicyclo[n.1.0]alkanes [J].

Dolfen, Jeroen ;

Yadav, Nagendra Nath ;

De Kimpe, Norbert ;

D'hooghe, Matthias ;

Ha, Hyun-Joon .

ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (22) :3485-3511

[17] Tethered aminohydroxylation: Dramatic improvements to the process [J].

Donohoe, Timothy J. ;

Bataille, Carole J. R. ;

Gattrell, William ;

Kloesges, Johannes ;

Rossignol, Emilie .

ORGANIC LETTERS, 2007, 9 (09) :1725-1728

[18] Competitive Ring Expansion of Azetidines into Pyrrolidines and/or Azepanes [J].

Drouillat, Bruno ;

Dorogan, Igor V. ;

Kletskii, Mikhail ;

Burov, Oleg N. ;

Couty, Francois .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (15) :6677-6685

[19] Insight into the Regioselectivity of Nucleophilic Ring-Opening of Azetidinium Ions Containing Quaternary Carbon Atoms [J].

Drouillat, Bruno ;

Wright, Karen ;

David, Olivier ;

Couty, Francois .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (30) :6005-6012

[20] New synthesis of chiral 1,3-oxazinan-2-ones from carbohydrate derivatives [J].

Ella-Menye, JR ;

Sharma, V ;

Wang, GJ .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (02) :463-469

← 1 2 3 4 5 6 7 →