Microwave-Assisted Synthesis of 2-Methyl-1H-indole-3-carboxylate Derivatives via Pd-Catalyzed Heterocyclization

被引：6

作者：

Bellavita, Rosa ^{[1
,2
]}

Casertano, Marcello ^{[1
,2
]}

Grasso, Nicola ^{[1
,2
]}

Gillick-Healy, Malachi ^{[2
]}

Kelly, Brian G. ^{[2
]}

Adamo, Mauro F. A. ^{[2
,3
]}

Menna, Marialuisa ^{[1
]}

Merlino, Francesco ^{[1
]}

Grieco, Paolo ^{[1
]}

机构：

[1] Univ Naples Federico II, Dept Pharm, Via D Montesano 49, I-80131 Naples, Italy

[2] KelAda Pharmachem Ltd, A1-01, Dublin D04, Ireland

[3] Royal Coll Surgeons Ireland, Ctr Synth & Chem Biol, Dept Chem, 123 St Stephens Green, Dublin D02 YN77, Ireland

来源：

SYMMETRY-BASEL | 2022年 / 14卷 / 03期

关键词：

indoles; C-H activation; Pd-catalyzed coupling; microwave irradiation; N-aryl enamines; N BOND FORMATION; OXIDATIVE CYCLIZATION; BIOLOGICAL EVALUATION; ARYL ENAMINES; INDOLE; DESIGN; CHEMISTRY; POTENT;

D O I：

10.3390/sym14030435

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

Indole moiety is well-known as a superlative framework in many natural products and synthetic pharmaceuticals. Herein, we report an efficient procedure to synthesize a series of functionalized 2-methyl-1H-indole-3-carboxylate derivatives from commercially available anilines properly functionalized by different electron-withdrawing and -donating groups through a palladium-catalyzed intramolecular oxidative coupling. The conversion of a variety of enamines into the relevant indole was optimized by exposing the neat mixture of reactants to microwave irradiation, obtaining the desired products in excellent yields and high regioselectivity. The synthesized compounds were confirmed by H-1 and C-13 spectroscopic means as well as by high-resolution mass spectrometry.

引用

页数：11

共 37 条

[1] Design, synthesis, and biological evaluation of substituted-N-(thieno[2,3-b]pyridin-3-yl)-guanidines, N-(1H-pyrrolo[2,3-b]pyridin-3-yl)-guanidines, and N-(1H-indol-3-yl)-guanidines [J].