Synthesis of Polysubstituted 2-Aminoimidazoles via Alkene-Diamination of Guanidine with Conjugated α-Bromoalkenones

被引：14

作者：

Guchhait, Sankar K. ^{[1
]}

Hura, Neha ^{[1
]}

Shah, Archana P. ^{[1
]}

机构：

[1] NIPER, Dept Med Chem, Sector 67,SAS Nagar, Mohali 160062, Punjab, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 05期

关键词：

INTRAMOLECULAR DIAMINATION; IMIDAZOLES; PALLADIUM; AMIDINES; HETEROCYCLES; ALKALOIDS; CHEMISTRY; OXIDATION; BROMIDE; KETONES;

D O I：

10.1021/acs.joc.6b03021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A step-economical access to polysubstituted aminoimidazoles has been accomplished via alkene vicinal C-N bonds formation of 2-bromo-2-alkenones with guanidine avoiding its NH-protection/derivatization prerequisite for electronic modulation. The approach has excellent substrate scope, is amenable to diverse guanidine-containing substrates, and introduces distinctive substitutions/functionalities into aminoimidazole core. It is also applicable to preparation of fused-imidazoles. The reaction involves a tandem pathway of azaMichael addition, S(N)2, and a unique redox-neutral process, as evident by spectroscopic study and control experiments.

引用

页码：2745 / 2752

页数：8

共 50 条

[1] The tethered Biginelli condensation in natural product synthesis [J].

Aron, ZD ;

Overman, LE .

CHEMICAL COMMUNICATIONS, 2004, (03) :253-265

[2] The coordination chemistry of guanidines and guanidinates [J].

Bailey, PJ ;

Pace, S .

COORDINATION CHEMISTRY REVIEWS, 2001, 214 :91-141

[3] Flexible Synthesis of Pyrimidines with Chiral Monofluorinated and Difluoromethyl Side Chains [J].

Bannwarth, Pierre ;

Valleix, Alain ;

Gree, Danielle ;

Gree, Rene .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (12) :4646-4649

[4] Switch in Site of Inhibition: A Strategy for Structure-Based Discovery of Human Topoisomerase IIα Catalytic Inhibitors [J].

Baviskar, Ashish T. ;

Amrutkar, Suyog M. ;

Trivedi, Neha ;

Chaudhary, Vikas ;

Nayak, Anmada ;

Guchhait, Sankar K. ;

Banerjee, Uttam C. ;

Bharatam, Prasad V. ;

Kundu, Chanakya N. .

ACS MEDICINAL CHEMISTRY LETTERS, 2015, 6 (04) :481-485

[5] Natural guanidine derivatives [J].

Berlinck, RGS ;

Kossuga, MH .

NATURAL PRODUCT REPORTS, 2005, 22 (04) :516-550

[6] α-Bromination of linear enals and cyclic enones [J].

Bovonsombat, Pakorn ;

Rujiwarangkul, Rungkarn ;

Bowornkiengkai, Thanathip ;

Leykajarakul, Juthamard .

TETRAHEDRON LETTERS, 2007, 48 (49) :8607-8610

[7]

Cardona F, 2009, NAT CHEM, V1, P269, DOI [10.1038/nchem.256, 10.1038/NCHEM.256]

[8] Novel Combretastatin-2-aminoimidazole Analogues as Potent Tubulin Assembly Inhibitors: Exploration of Unique Pharmacophoric Impact of Bridging Skeleton and Aryl Moiety [J].

Chaudhary, Vikas ;

Venghateri, Jubina B. ;

Dhaked, Hemendra P. S. ;

Bhoyar, Anil S. ;

Guchhait, Sankar K. ;

Panda, Dulal .

JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (07) :3439-3451

[9] KETENE-S,S-ACETALS .6. SYNTHESIS OF 3,3-BIS-(METHYLTHIO)-2-PROPENE-2-ALKYL-1-ARYL-1-ONES AND THEIR REACTION WITH GUANIDINE - NOVEL ROUTE FOR PYRIMIDINE SYNTHESIS [J].

CHAUHAN, SMS ;

JUNJAPPA, H .

TETRAHEDRON, 1976, 32 (15) :1911-1916

[10] Metal-free diamination of alkenes employing bromide catalysis [J].

Chavez, Patricia ;

Kirsch, Jonathan ;

Hoevelmann, Claas H. ;

Streuff, Jan ;

Martinez-Belmonte, Marta ;

Escudero-Adan, Eduardo C. ;

Martin, Eddy ;

Muniz, Kilian .

CHEMICAL SCIENCE, 2012, 3 (07) :2375-2382

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