A metal-free tandem dehydrogenative α-arylation reaction of propargylic alcohols with 2-alkynylbenzaldoximes toward the synthesis of α-(4-bromo-isoquinolin-1-yl)-propenone skeletons

被引：0

作者：

Alatat, Khalil ^{[1
]}

Kejani, Alireza Abbasi ^{[1
]}

Nikbakht, Ali ^{[1
]}

Bijanzadeh, Hamid Reza ^{[2
]}

Balalaie, Saeed ^{[1
,3
]}

机构：

[1] KN Toosi Univ Technol, Peptide Chem Res Inst, POB 15875-4416, Tehran, Iran

[2] Tarbiat Modares Univ, Fac Nat Resources & Marine Sci, Dept Environm Sci, Tehran, Iran

[3] Kermanshah Univ Med Sci, Med Biol Res Ctr, Kermanshah, Iran

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2022年 / 20卷 / 03期

基金：

美国国家科学基金会;

关键词：

TRIFLATE-CATALYZED REACTION; ALL-CARBON OLEFINS; STEREOSELECTIVE-SYNTHESIS; FACILE SYNTHESIS; ALKYNES; ELIMINATION; REARRANGEMENT; GENERATION; REAGENTS; ALKENES;

D O I：

10.1039/d1ob02114a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A tandem reaction of 2-alkynylbenzaldoximes with propargylic alcohols has been developed for the synthesis of alpha-(4-bromo-isoquinolin-1-yl)-propenones. Employing 2-alkynylbenzaldoximes as a precursor in the presence of Br-2 generates 4-bromo-isoquinoline-N-oxides. Subsequently, dehydroxylation of propargylic alcohols gives carbocation intermediates, which are trapped using the N-oxides, affording aryl-substituted alpha-enones.

引用

页码：579 / 583

页数：5

共 28 条

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[2] Synthesis of 2-(Isoquinolin-1-yl)prop-2-en-1-ones via Silver(I)-Catalyzed One-Pot Tandem Reaction of ortho-Alkynylbenzaldoximes with Propargylic Alcohols
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