Metal-free approach for imidazole synthesis via one-pot N-α-C(sp3)-H bond functionalization of benzylamines

被引：2

作者：

Kadu, Vikas D. ^{[1
]}

Thokal, Machhindra S. ^{[1
]}

Godase, Rajkumar K. ^{[1
]}

Kotali, Bhagyashree C. ^{[1
]}

Wadkar, Pooja S. ^{[1
]}

机构：

[1] Punyashlok Ahilyadevi Holkar Solapur Univ, Sch Chem Sci, Solapur 413255, Maharashtra, India

来源：

RSC ADVANCES | 2024年 / 14卷 / 39期

关键词：

TETRASUBSTITUTED IMIDAZOLES; POLYSUBSTITUTED IMIDAZOLES; NITROGEN-HETEROCYCLES; EFFICIENT; ANTIBACTERIAL; CYCLIZATION; ANALOGS; DRUGS;

D O I：

10.1039/d4ra03939d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A metal-free one-pot method is established for the synthesis of tetrasubstituted imidazoles from the reaction of arylmethylamines and 1,2-dicarbonyls/benzoin. The N-alpha-C(sp(3))-H bond functionalization of arylmethylamines using a catalytic amount of AcOH afforded polysubstituted imidazoles under aerobic conditions in significant yields of up to 95%.

引用

页码：28332 / 28339

页数：8

共 53 条

[1] Polysubstituted Imidazoles as LysoTracker Molecules: Their Synthesis via Iodine/H2O and Cell-Imaging Studies [J].

Adhikary, Saswati ;

Majumder, Leena ;

Pakrashy, Sourav ;

Srinath, Ravuri ;

Mukherjee, Kaustuv ;

Mandal, Chitra ;

Banerji, Biswadip .

ACS OMEGA, 2020, 5 (24) :14394-14407

[2] Imidazole-based fluorophores: Synthesis and applications [J].

Al Sharif, O. F. ;

Nhari, L. M. ;

El-Shishtawy, R. M. ;

Asiri, A. M. .

MATERIALS TODAY CHEMISTRY, 2023, 29

[3]

Al-Majed Abdul-Rahman A, 2015, Profiles Drug Subst Excip Relat Methodol, V40, P159, DOI 10.1016/bs.podrm.2015.02.003

[4] Imidazole as a Promising Medicinal Scaffold: Current Status and Future Direction [J].

Alghamdi, Sahar S. ;

Suliman, Rasha S. ;

Almutairi, Khlood ;

Kahtani, Khawla ;

Aljatli, Dimah .

DRUG DESIGN DEVELOPMENT AND THERAPY, 2021, 15 :3289-3312

[5] Analogues of 4,5-bis(3,5-dichlorophenyl)-2-trifluoromethyl-1H-imidazole as potential antibacterial agents. [J].

Antolini, M ;

Bozzoli, A ;

Ghiron, C ;

Kennedy, G ;

Rossi, T ;

Ursini, A .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (07) :1023-1028

[6] A facile and efficient method for the synthesis of 1,2,4-trisubstituted imidazoles with enamides and benzylamines [J].

Cao, Jinhui ;

Zhou, Xiaoqiang ;

Ma, Haojie ;

Shi, Chong ;

Huang, Guosheng .

RSC ADVANCES, 2016, 6 (62) :S7232-S7235

[7] Elemental Sulfur-Promoted Aerobic Cyclization of Ketones and Aliphatic Amines for Synthesis of Tetrasubstituted Imidazoles [J].

Chen, Xiangui ;

Wang, Zhen ;

Huang, Huawen ;

Deng, Guo-Jun .

ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (20) :4017-4022

[8]

Chopra Pratiksha N., 2020, Current Drug Discovery Technologies, V17, P574, DOI 10.2174/1570163816666190320123340

[9] An efficient synthesis of tetrasubstituted imidazoles from N-(2-oxo)-amides [J].

Claiborne, CF ;

Liverton, NJ ;

Nguyen, KT .

TETRAHEDRON LETTERS, 1998, 39 (49) :8939-8942

[10]

De Luca L, 2006, CURR MED CHEM, V13, P1

← 1 2 3 4 5 6 →