Catalyst-Free Synthesis of Functionalized 4-Substituted-4H-Benzo[d][1,3]oxazines via Intramolecular Cyclization of ortho-Amide-N-tosylhydrazones

被引：2

作者：

Yan, Jun ^{[1
]}

Tran, Christine ^{[1
]}

Retailleau, Pascal ^{[2
]}

Alami, Mouad ^{[1
]}

Hamze, Abdallah ^{[1
]}

机构：

[1] Univ Paris Saclay, CNRS, BioCIS, F-91400 Orsay, France

[2] Univ Paris Saclay, Inst Chim Subst Nat, CNRS, UPR 2301, F-91198 Gif Sur Yvette, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 13期

关键词：

AEROBIC OXIDATIVE SYNTHESIS; VERSATILE REAGENTS; CARBOXYLIC-ACIDS; BOND FORMATION; 4H-3,1-BENZOXAZINES; UPDATE; AMINES; ETHERS; ROUTE;

D O I：

10.1021/acs.joc.3c00534

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Functionalized 4-aryl-4H-benzo[d][1,3]oxazines are synthesized under transition-metal-freeconditionsusing ortho-amide-N-tosylhydrazones.This synthetic method uses readily available N-tosylhydrazonesas the diazo compound precursors and involves an intramolecular ringclosure reaction mediated by a protic polar additive (iPrOH). A wide range of functionalized oxazines are obtained by thisstraightforward method in good to excellent yields. Furthermore, theviability of our strategy is illustrated by the gram-scale elaborationof a bromo-substituted 4H-benzo[d][1,3]oxazine and its post-functionalization by palladium-catalyzedcross-couplings.

引用

页码：8636 / 8642

页数：7

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