Photochemical Michael Addition of Indoles to α,β-Unsaturated Ketones utilizing Arylazo Sulfones as the Photoacid Generators

被引：3

作者：

Galathri, Eirini M. ^{[1
]}

Di Terlizzi, Lorenzo ^{[2
]}

Fagnoni, Maurizio ^{[2
]}

Protti, Stefano ^{[2
]}

Kokotos, Christoforos G. ^{[1
]}

机构：

[1] Natl & Kapodistrian Univ Athens, Dept Chem, Lab Organ Chem, Athens 15771, Greece

[2] Univ Pavia, Dept Chem, PhotoGreen Lab, Viale Taramelli 12, I-27100 Pavia, Italy

来源：

CHEMCATCHEM | 2024年 / 16卷 / 18期

关键词：

photoacid generators (PAGs); photochemistry; Michael addition; alpha; beta-unsaturated ketones; arylazo sulfones; FRIEDEL-CRAFTS ALKYLATION; CATALYZED CONJUGATE ADDITION; IONIC LIQUID; HETEROGENEOUS CATALYST; ACIDS; HYDROACYLATION; LACTONES; WATER;

D O I：

10.1002/cctc.202400686

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The Michael-type addition of indoles represents one of the most important C-C bonds forming reactions at their C-3 position. Herein, we present a mild, versatile and sustainable protocol for the efficient preparation of beta-indolylketones via a Michael addition between indoles and chalcones or alpha,beta-unsaturated ketones in the presence of substituted arylazo sulfones as photoacid generators (PAGs).

引用

页数：5

共 50 条

[21] Green, efficient and practical Michael addition of arylamines to α,β-unsaturated ketones
Jiang, Ran
Li, Dan-Hua
Jiang, Jing
Xu, Xiao-Ping
Chen, Tao
Ji, Shun-Jun
TETRAHEDRON, 2011, 67 (20) : 3631 - 3637
[22] On the Michael Addition of Water to a, αβ-Unsaturated Ketones Using Amino Acids
Resch, Verena
Seidler, Christiane
Chen, Bi-Shuang
Degeling, Ian
Hanefeld, Ulf
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (34) : 7697 - 7704
[23] Gallium(III) triiodide catalyzed conjugate addition of indoles with α,β-unsaturated ketones
Huang, Zhi-Hao
Zou, Han-Ping
Jiang, Wen-Qing
TETRAHEDRON LETTERS, 2006, 47 (45) : 7965 - 7968
[24] Influence of the Reaction Conditions on the Evolution of the Michael Addition of β-Keto Sulfones to α,β-Unsaturated Aldehydes
Aleman, Jose
Marcos, Vanesa
Marzo, Leyre
Garcia Ruano, Jose Luis
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (23) : 4482 - 4491
[25] The Michael addition of indoles and pyrrole to α-, β-unsaturated ketones and double-conjugate 1,4-addition of indoles to symmetric enones promoted by pulverization-activation method and Thia-Michael addition catalyzed by wet cyanuric chloride
Ghorbani-Vaghei, Ramin
Veisi, Hojat
MOLECULAR DIVERSITY, 2010, 14 (02) : 385 - 392
[26] The Michael addition of indoles and pyrrole to α-, β-unsaturated ketones and double-conjugate 1,4-addition of indoles to symmetric enones promoted by pulverization-activation method and Thia-Michael addition catalyzed by wet cyanuric chloride
Ramin Ghorbani-Vaghei
Hojat Veisi
Molecular Diversity, 2010, 14 : 385 - 392
[27] The Michael addition of indole to α,β-unsaturated ketones catalyzed by iodine at room temperature
Wang, SY
Ji, SJ
Loh, TP
SYNLETT, 2003, (15) : 2377 - 2379
[28] Michael addition of dimedone with α,β-unsaturated ketones:: Synthesis of quinoline and chromene derivatives
Kendre, Dhananjay B.
Toche, Raghunath B.
Jachak, Madhukar N.
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 45 (03) : 667 - 671
[29] Highly Enantioselective Organocatalytic Sulfa-Michael Addition to α,β-Unsaturated Ketones
Rana, Nirmal K.
Selvakumar, Sermadurai
Singh, Vinod K.
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (06): : 2089 - 2091
[30] ADDITION AND ANNULATION REACTIONS BETWEEN INDOLES AND ALPHA,BETA-UNSATURATED KETONES
GARNICK, RL
LEVERY, SB
LEQUESNE, PW
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (06): : 1226 - 1229

← 1 2 3 4 5 →