C2-Arylated Indoles and Benzofurans through Formal (4+1) Annulation of N-Sulfonyl-2-aminobenzaldehydes and Salicylaldehyde Derivatives with Electron-Deficient Benzyl Chlorides

被引：0

作者：

van Capelle, Lillian A. de Ceuninck ^{[1
]}

Rahmannia, Kimia ^{[1
]}

Macdonald, James M. ^{[2
]}

Richardson, Christopher ^{[1
]}

Gardiner, Michael G. ^{[3
]}

Ryan, John H. ^{[2
]}

Babaahmadi, Rasool ^{[4
]}

Wales, Steven M. ^{[1
]}

Hyland, Christopher J. T. ^{[1
]}

机构：

[1] Univ Wollongong, Mol Horizons Res Inst, Sch Chem & Mol Biosci, Wollongong, NSW 2522, Australia

[2] CSIRO, Biomed Mfg Program, Res Way, Clayton, Vic 3168, Australia

[3] Australian Natl Univ, Res Sch Chem, Acton, ACT 2601, Australia

[4] Cardiff Univ, Sch Chem, Cardiff CF10 3AT, Wales

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 23期

基金：

澳大利亚研究理事会;

关键词：

N-THIOPHOSPHINYL IMINES; O-QUINONE METHIDES; C-H ACTIVATION; DOMINO REACTION; SULFUR YLIDES; STEREOSELECTIVE-SYNTHESIS; ANTIMICROBIAL EVALUATION; FACILE SYNTHESIS; IMIDAMIDES; TRANS-2,3-DIHYDROBENZOFURANS;

D O I：

10.1021/acs.joc.4c02231

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A two-step formal (4 + 1) annulation-dehydration reaction offers a convenient route to C2-arylated indoles and benzofurans. This reaction exploits the bifunctional reactivity of electron-deficient benzyl chlorides with N-sulfonyl-2-aminobenzaldehydes or salicylaldehyde derivatives. The reaction tolerates both electron-withdrawing and donating groups on the substituted aldehydes, as well as variation of electron-withdrawing groups at the para position of the benzyl chloride reagent. This work also identifies interesting byproducts resulting from the self-reaction of these benzyl chlorides under basic conditions.

引用

页码：17488 / 17501

页数：14

共 6 条

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[3] Organocatalytic Enantioselective [1+4] Annulation of Morita-Baylis Hillman Carbonates with Electron-Deficient Olefins: Access to Chiral 2,3-Dihydrofuran Derivatives
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[5] Selective Functionalization of Aromatic C(sp2)-H Bonds in the Presence of Benzylic C(sp3)-H Bonds by Electron-Deficient Carbenoids Generated from 4-Acyl-1-Sulfonyl-1,2,3-Triazoles
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[6] STEREOCHEMICAL INVESTIGATION OF 3 47-ELECTRON CARBONYL, NITRENE BICAPPED TRIMETAL CLUSTERS IN THE HOMOLOGOUS 48/47-ELECTRON [CO3(ETA-5-C5ME5)3-X(ETA-5-C5H4ME)X(MU-3-CO)(MU-3-NH)]N SERIES (X = 0, 1, 2 - N = 0, + 1) - BONDING ANALYSIS OF THE REDOX-GENERATED CHANGES IN GEOMETRY UPON FORMATION OF ELECTRON-DEFICIENT SPECIES BY OXIDATION OF TRIANGULARLY BONDED 48-ELECTRON METAL-CLUSTERS CONTAINING PI-ACCEPTOR CARBONYL CAPPING LIGANDS
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