Hydrogen-Bond-Catalyzed Arylationof 3-(Aminoalkyl)indoles via C-N Bond Cleavage with Thiourea under Microwave Irradiation: An Approach to 3-(α,α-Diarylmethyl) indoles

被引：24

作者：

Deb, Mohit L. ^{[1
]}

Das, Churnika ^{[1
]}

Deka, Bhaskar ^{[1
]}

Saikia, Prakash J. ^{[2
]}

Baruah, Pranjal K. ^{[1
]}

机构：

[1] Gauhati Univ, Dept Appl Sci, GUIST, Gauhati 781014, Assam, India

[2] Analyt Chem Div CSIR NEIST, Jorhat 785006, Assam, India

来源：

SYNLETT | 2016年 / 27卷 / 20期

关键词：

hydrogen-bond-catalyzed; thiourea; microwave; indoles; vinylogous iminium ion; 3-AMINO ALKYLATED INDOLES; MANNICH-TYPE REACTION; MULTICOMPONENT SYNTHESIS; ANTIOXIDANT ACTIVITIES; MICHAEL ADDITION; DERIVATIVES; CHEMISTRY;

D O I：

10.1055/s-0036-1588887

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed a simple and efficient method for the arylation of 3-(aminoalkyl) indoles with aryl alcohols and other aromatic nucleophiles through C-N bond cleavage under microwave irradiation to synthesize 3-(alpha, alpha-diarylmethyl) indoles. The method uses thiourea as catalyst, which is environmentally benign, water-tolerant and easy to handle. Notably, acid-sensitive substrates are tolerated under the reaction conditions. Thiourea activates the tertiary amine through double hydrogen bonding and converts it into a better leaving group. The reaction proceeds through the formation of vinylogous iminium ion as an intermediate.

引用

页码：2788 / 2794

页数：7

共 56 条

[1] Novel routes to pyrroles, indoles and carbazoles -: Applications in natural product synthesis [J].

Agarwal, S ;

Cämmerer, S ;

Filali, S ;

Fröhner, W ;

Knöll, J ;

Krahl, MP ;

Reddy, KR ;

Knölker, HJ .

CURRENT ORGANIC CHEMISTRY, 2005, 9 (15) :1601-1614

[2] THE SYNTHESIS OF TRYPTOPHAN FROM GRAMINE [J].

ALBERTSON, NF ;

ARCHER, S ;

SUTER, CM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1945, 67 (01) :36-37

[3] REACTIONS OF OPTICALLY ACTIVE INDOLE MANNICH BASES [J].

ALBRIGHT, JD ;

SNYDER, HR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (09) :2239-2245

[4]

[Anonymous], 2010, INT J CHEM TECH RES

[5]

[Anonymous], [No title captured]

[6] Structure-activity relationships for antioxidant activities of a series of flavonoids in a liposomal system [J].

Arora, A ;

Nair, MG ;

Strasburg, GM .

FREE RADICAL BIOLOGY AND MEDICINE, 1998, 24 (09) :1355-1363

[7] Antioxidant Activities of Retinoidal Benzimidazole Or Indole Derivatives in In Vitro Model Systems [J].

Ates-Alagoz, Zeynep .

CURRENT MEDICINAL CHEMISTRY, 2013, 20 (36) :4633-4639

[8] A novel ring-substituted diindolylmethane, 1,1-bis[3′-(5-methoxyindolyl)]-1-(p-t-butylphenyl) methane, inhibits extracellular signal-regulated kinase activation and induces apoptosis in acute myelogenous leukemia [J].

Contractor, R ;

Samudio, IJ ;

Estrov, Z ;

Harris, D ;

McCubrey, JA ;

Safe, SH ;

Andreeff, M ;

Konopleva, M .

CANCER RESEARCH, 2005, 65 (07) :2890-2898

[9] Copper-Catalyzed Regioselective Intramolecular Oxidative α-Functionalization of Tertiary Amines: An Efficient Synthesis of Dihydro-1,3-Oxazines [J].

Deb, Mohit L. ;

Dey, Suvendu S. ;

Bento, Isabel ;

Teresa Barros, M. ;

Maycock, Christopher D. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (37) :9791-9795

[10] Dynamic pharmacophore model optimization: Identification of novel HIV-1 integrase inhibitors [J].

Deng, JX ;

Sanchez, T ;

Neamati, N ;

Briggs, JM .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (05) :1684-1692

← 1 2 3 4 5 6 →