Synlett 2014; 25(15): 2115-2120
DOI: 10.1055/s-0034-1378446
letter
© Georg Thieme Verlag Stuttgart · New York

Metal-Free One-Pot Protocol for the Preparation of Unexpected Carbazole Derivative in Water: Easy Access to Pyrimidocarbazole and Pyridocarbazolone Derivatives

Soumen Biswas
Discipline of Chemistry, Indian Institute of Technology Indore, Madhya Pradesh, 452017, India   Fax: +91(731)2364182   Email: sampaks@iiti.ac.in
,
Debashis Majee
Discipline of Chemistry, Indian Institute of Technology Indore, Madhya Pradesh, 452017, India   Fax: +91(731)2364182   Email: sampaks@iiti.ac.in
,
Anuradha Dagar
Discipline of Chemistry, Indian Institute of Technology Indore, Madhya Pradesh, 452017, India   Fax: +91(731)2364182   Email: sampaks@iiti.ac.in
,
Sampak Samanta*
Discipline of Chemistry, Indian Institute of Technology Indore, Madhya Pradesh, 452017, India   Fax: +91(731)2364182   Email: sampaks@iiti.ac.in
› Author Affiliations
Further Information

Publication History

Received: 12 May 2014

Accepted after revision: 12 June 2014

Publication Date:
29 July 2014 (online)


Abstract

A novel, one-pot, metal-free-based catalytic system for the synthesis of a series of functionalized 1-methoxycarbonyl-2-aryl/alkyl-9H-carbazole derivatives has been successfully achieved in water medium by the combination of methyl 2-(3-formyl-1H-­indol-2-yl)acetate with aryl/alkyl-substituted β-acroleins using DABCO (20 mol%), followed by treatment of HCl under air at heating conditions. This sequential one-pot protocol provides moderate to good yields (51–68%) of aforesaid compounds. In addition, biologically important carbazole-fused new heterocyclic scaffolds can be synthesized through our procedure.

Supporting Information

 
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