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

[21] Transition metal-free diastereospecific synthesis of (Z)-2-arylidene-2,3-dihydrobenzo[b][1,4]dioxines by reaction of (Z)-1,2-dibromo-3-aryl-2-propenes with catechols
Rekowski, Szymon P.
Wani, Aabid A.
Conrad, Juergen
Bharatam, Prasad, V
Frey, Wolfgang
Beifuss, Uwe
TETRAHEDRON, 2020, 76 (42)
[22] I2-Induced Metal-Free C(sp2)-H Functionalization of Indoles via One-Pot and Two-Step Reaction with 1-(2-Hydroxyphenyl)-propargyl Alcohols: Access to 3-(Benzofuran-3-yl)-1H-indoles
Zhu, Yang
Deng, Guisheng
JOURNAL OF ORGANIC CHEMISTRY, 2025,
[23] One-Pot Synthesis of [1,2,3]Triazolo[1,5-a]quinoxalin-4(5H)-ones by a Metal-Free Sequential Ugi-4CR/Alkyne-Azide Cycloaddition Reaction
Yan, Yan-Mei
Li, Hao-Yang
Zhang, Min
Wang, Rong-Xin
Zhou, Chen-Guang
Ren, Zhen-Xing
Ding, Ming-Wu
SYNLETT, 2020, 31 (01) : 73 - 76
[24] Metal-free, zinc(II) and lead(II) phthalocyanines functioning with 3-(2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenethyl methacrylate groups: Synthesis and investigation of photophysical and photochemical properties
Demirbas, Umit
Piskin, Mehmet
Barut, Burak
Bayrak, Riza
Durmus, Mahmut
Kantekin, Halit
SYNTHETIC METALS, 2016, 220 : 276 - 285
[25] Synthesis of 4-(Iso)Quinolinyl-3(2H)-furanones from (Iso)Quinoline N-oxides and 1,4-Diyn-3-ones: A Comparison of Copper Catalysis and Metal-free Reaction
Li, Xuetong
Wang, Tao
Zhang, Zunting
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (04) : 696 - 701
[26] Metal-free synthesis of 1,1-dimethyl-2,2,2-trifluoroethyl substituted quinazolinones via tandem radical cyclization of quinazolin-4(3H)-ones with 3,3,3-trifluoro-2,2-dimethylpropanoic acid
Gao, Shenyuan
Cai, Menglu
Wang, Xiaozhong
Jiang, Dapeng
Lin, Pen
Dai, Liyan
ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (31) : 6376 - 6384
[27] A facile metal-free one-flask synthesis of multi-substituted furans via a BF3•Et2O mediated formal [4+1] reaction of 3-chloro-3-phenyldiazirines and α,β-alkenyl ketones
Zhang, Zixin
Huang, Aimin
Ma, Lin
Xu, Jian-hua
Zhang, Min
RSC ADVANCES, 2022, 12 (24) : 15190 - 15195
[28] Synthesis and electrochemical, electrical and gas sensing properties of novel mononuclear metal-free, Zn(II), Ni(II), Co(II), Cu(II), Lu(III) and double-decker Lu(III) phthalocyanines substituted with 2-(2H-1,2,3-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl) phenoxy
Gumrukcu, Gulsah
Ozgur, Mahmure Ustun
Altindal, Ahmet
Ozkaya, Ali Riza
Salih, Bekir
Bekaroglu, Ozer
SYNTHETIC METALS, 2011, 161 (1-2) : 112 - 123

← 1 2 3 →