I2-Mediated [6+1] Annulation of Alkynes with MsONH3OTf: Direct Synthesis of Benzo[b]azepines

被引：2

作者：

Zhuang, Daijiao ^{[1
]}

Jiang, Shixuan ^{[1
]}

Wang, Youzhi ^{[2
]}

Wang, Xiajun ^{[2
]}

Shen, Siwei ^{[1
]}

Yan, Rulong ^{[1
]}

机构：

[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China

[2] Chengdu Guibao Sci & Technol Co Ltd, Chengdu 610041, Sichuan, Peoples R China

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 17期

关键词：

RING-EXPANSION; AMINATION; CYCLOADDITIONS; 1-BENZAZEPINES; CYCLIZATION; ALKENES;

D O I：

10.1021/acs.orglett.3c00790

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of benzo[b]azepines using protonated aminating reagent (MsONH3OTf) and alkynes through I2- mediated [6 + 1] annulation reaction has been developed. This protocol features excellent functional group tolerance and mild reaction conditions and affords the benzo[b]azepines in moderate to good yields under metal-free reaction conditions.

引用

页码：3007 / 3012

页数：6

共 23 条

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[4] I2-Mediated [3+2] annulation of methyl-azaarenes with alkyl 2-isocyanoacetates or amino acid ester hydrochlorides: selective synthesis of iodine-functionalized and non-iodine-functionalized fused imidazoles
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[7] Direct synthesis of 2-methylpyridines via I2-triggered [3+2+1] annulation of aryl methyl ketoxime acetates with triethylamine as the carbon source
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[9] Palladium-catalyzed one-pot synthesis of benzo[b][1,6]naphthyridines via Sonogashira coupling and annulation reactions from 2-chloroquinoline-3-carbonitriles
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[10] In(OTf)3-catalyzed tandem aza-Piancatelli rearrangement/Michael reaction for the synthesis of 3,4-dihydro-2H-benzo[b][1,4]thiazine and oxazine derivatives
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