Synthesis of α-amino amidines through molecular iodine-catalyzed three-component coupling of isocyanides, aldehydes and amines

被引：23

作者：

Adiyala, Praveen Reddy ^{[1
]}

Chandrasekhar, D. ^{[1
]}

Kapure, Jeevak Sopanrao ^{[1
]}

Reddy, Chada Narsimha ^{[1
]}

Maurya, Ram Awatar ^{[1
]}

机构：

[1] Indian Inst Chem Technol, CSIR, Div Med Chem & Pharmacol, Hyderabad 500007, Andhra Pradesh, India

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 10卷

关键词：

alpha-amino amidines; iodine; isocyanide; multicomponent reaction; Ugi reaction; UGI CONDENSATION REACTION; ETHYL DIAZOACETATE; IN-VITRO; INHIBITORS; CYCLOPROPANATION; CHEMISTRY; PYRAZINES; SEQUENCE; AMIDES;

D O I：

10.3762/bjoc.10.214

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile and efficient synthetic protocol for the synthesis of alpha-amino amidines has been developed using a molecular iodine-catalyzed three-component coupling reaction of isocyanides, amines, and aldehydes. The presented strategy offers the advantages of mild reaction conditions, low environmental impact, clean and simple methodology, high atom economy, wide substrate scope and high yields.

引用

收藏

页码：2065 / 2070

页数：6

相关论文

共 30 条

[1] Synthesis, DNA affinity, and Antiprotozoal activity of fused ring dicationic compounds and their prodrugs [J].

Arafa, RK ;

Brun, R ;

Wenzler, T ;

Tanious, FA ;

Wilson, WD ;

Stephens, CE ;

Boykin, DW .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (17) :5480-5488

[2] Highly efficient one-pot synthesis of N-sulfonylamidines by Cu-catalyzed three-component coupling of sulfonyl azide, alkyne, and amine [J].

Bae, I ;

Han, H ;

Chang, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (07) :2038-2039

[3] 3-Amidinopyridine (nicotinamidine) [J].

Barber, HJ ;

Slack, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1944, 66 :1607-1607

[4]

Bienaymé H, 1998, ANGEW CHEM INT EDIT, V37, P2234, DOI 10.1002/(SICI)1521-3773(19980904)37:16<2234::AID-ANIE2234>3.0.CO

[5]

2-R

[6] Parallel synthesis of 3-aminoimidazo[1,2-a]pyridines and pyrazines by a new three-component condensation [J].

Blackburn, C ;

Guan, B ;

Fleming, P ;

Shiosaki, K ;

Tsai, S .

TETRAHEDRON LETTERS, 1998, 39 (22) :3635-3638

[7] The Development of N-α-(2-Carboxyl)benzoyl-N5-(2-fluoro-1-iminoethyl)-L-ornithine Amide (o-F-amidine) and N-α-(2-Carboxyl)benzoyl-N5-(2-chloro-1-iminoethyl)-L-ornithine Amide (o-Cl-amidine) As Second Generation Protein Arginine Deiminase (PAD) Inhibitors [J].

Causey, Corey P. ;

Jones, Justin E. ;

Slack, Jessica L. ;

Kamei, Daisuke ;

Jones, Larry E., Jr. ;

Subramanian, Venkataraman ;

Knuckley, Bryan ;

Ebrahimi, Pedram ;

Chumanevich, Alexander A. ;

Luo, Yuan ;

Hashimoto, Hiroshi ;

Sato, Mamoru ;

Hofseth, Lorne J. ;

Thompson, Paul R. .

JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (19) :6919-6935

[8] Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].

Dömling, A .

CHEMICAL REVIEWS, 2006, 106 (01) :17-89

[9] Minor groove DNA binders as antimicrobial agents.: 1.: Pyrrole tetraamides are potent antibacterials against vancomycin resistant Enteroccoci and methicillin resistant Staphylococcus aureus [J].

Dyatkina, NB ;

Roberts, CD ;

Keicher, JD ;

Dai, YQ ;

Nadherny, JP ;

Zhang, WT ;

Schmitz, U ;

Kongpachith, A ;

Fung, K ;

Novikov, AA ;

Lou, L ;

Velligan, M ;

Khorlin, AA ;

Chen, MS .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (04) :805-817

[10] Facile Synthesis of Sulfonyl Amidines and β-Amino Sulfonyl Enamines under Transition-Metal-Free Conditions [J].

Gao, Tingting ;

Zhao, Mingming ;

Meng, Xu ;

Li, Chuanbin ;

Chen, Baohua .

SYNLETT, 2011, (09) :1281-1284