A catalyst- and solvent-free multicomponent synthesis of 7-azagramine analogues via a Mannich type reaction

被引：16

作者：

Dongare, Sakharam B. ^{[1
]}

Chavan, Hemant V. ^{[2
]}

Bhale, Pravin S. ^{[1
]}

Mule, Yoginath B. ^{[1
]}

Kotmale, Amol S. ^{[1
]}

Bandgar, Babasaheb P. ^{[1
]}

机构：

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

[2] ASP Coll, Dept Chem, Dist Ratnagiri 415804, Maharashtra, India

来源：

CHINESE CHEMICAL LETTERS | 2016年 / 27卷 / 01期

关键词：

Bioisosters; 7-Azaindole; Mannich reaction; Multicomponent reaction; 3-AMINOALKYLATED INDOLES; ONE-POT; COMPONENT SYNTHESIS; PRACTICAL SYNTHESIS; EFFICIENT; DERIVATIVES; 7-AZAINDOLE; AZAINDOLES; INHIBITORS; ALKALOIDS;

D O I：

10.1016/j.cclet.2015.07.029

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A catalyst- and solvent-free protocol for the synthesis of 7-azagramine analogues is described via a three-component Mannich type reaction between 7-azaindole, aromatic aldehydes and heterocyclic amines in acceptable to excellent yields. Structures of the compounds were confirmed satisfactorily by H-1 NMR, IR, mass, TOCSY, HSQC and HMBC spectral analyses. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

引用

页码：99 / 103

页数：5

共 47 条

[1] A practical synthesis of 7-azaindolylcarboxy-endo-tropanamide (DF 1012)
Allegretti, M
Anacardio, R
Cesta, MC
Curti, R
Mantovanini, M
Nano, G
Topai, A
Zampella, G
[J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2003, 7 (02) : 209 - 213
[2] Bamborough P., 2008, [No title captured], Patent No. [2008034860A1, 2008034860]
[3] Uncatalyzed Knoevenagel condensation in PEG-600 at room temperature
Bandgar, Babasaheb P.
Korbad, Balaji L.
Patil, Sachin A.
Bandgar, Sunita B.
Chavan, Hemant V.
Hote, Baliram S.
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 2008, 61 (09) : 700 - 703
[4] Banfi L., 2005, Organic Reactions, V65, P1, DOI [10.1002/0471264180.or065.01, DOI 10.1002/0471264180.0R065.01]
[5] Novel indole and azaindole (pyrrolopyridine) cannabinoid (CB) receptor agonists: Design, synthesis, structure-activity relationships, physicochemical properties and biological activity
Blaazer, Antoni R.
Lange, Jos H. M.
van der Neut, Martina A. W.
Mulder, Arie
den Boon, Femke S.
Werkman, Taco R.
Kruse, Chris G.
Wadman, Wytse J.
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (10) : 5086 - 5098
[6] Efficient and solvent-free synthesis of bis-indolylmethanes using silica gel supported aluminium chloride as a reusable catalyst
Boroujeni, Kaveh Parvanak
Parvanak, Kamran
[J]. CHINESE CHEMICAL LETTERS, 2011, 22 (08) : 939 - 942
[7] Higher-order multicomponent reactions: beyond four reactants
Brauch, Sebastian
van Berkel, Sander S.
Westermann, Bernhard
[J]. CHEMICAL SOCIETY REVIEWS, 2013, 42 (12) : 4948 - 4962
[8] Recent advances on organocatalysed asymmetric Mannich reactions
Cai, Xiao-hua
Xie, Bing
[J]. ARKIVOC, 2013, : 264 - 293
[9] Synthesis of 2,4,5-triaryl and 1,2,4,5-tetraaryl imidazoles using silica chloride as an efficient and recyclable catalyst under solvent-free conditions
Chavan, Hemant V.
Narale, Dattatraya K.
[J]. COMPTES RENDUS CHIMIE, 2014, 17 (10) : 980 - 984
[10] Aqueous Extract of Acacia concinna Pods: An Efficient Surfactant Type Catalyst for Synthesis of 3-Carboxycoumarins and Cinnamic Acids via Knoevenagel Condensation
Chavan, Hemant V.
Bandgar, Babasaheb P.
[J]. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2013, 1 (08): : 929 - 936

← 1 2 3 4 5 →