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Title: Synthesis of Biologically Active Pyridoimidazole/Imidazobenzothiazole Annulated Polyheterocycles using Cyanuric Chloride in water
Authors: Pandey, A K
Sharma, Rashmi
Singh, Awantika
Shukla, Sanjeev
Srivastava, Kumkum
Puri, S K
Kumar, Brijesh
Chauhan, P M S
Keywords: Cyanuric Chloride;Heterocycles;Imidazobenzothiazole;Pictet-Spengler Reaction;Pyridoimidazole;Tetra-N-Butylammonium Bromide (TBAB)
Issue Date: 2014
Description: An efficient and mild protocol for rapid access to N-fused polyheterocycles via Pictet-Spengler type 6-endo cyclization using cyanuric chloride in aqueous reaction medium has been developed. The protocol is successfully applied to a wide range of aryl/heteroaryl aldehydes (8a-o), ketones (10a-e), electron rich metallocene aldehyde (8e) and indoline-2,3-diones (12a-c) using cyanuric chloride (15-20 mol %) with tetra-n-butylammonium bromide (TBAB) (2.0 equiv.) as an additive at 80-90 ˚C to give polyheterocycles in good to excellent yield (66-92%). Moreover some of the synthesized compounds were found to exhibit antiplasmodial activity against chloroquine sensitive (CQ-S) 3D7 and chloroquine resistant (CQ-R) K1 strains of Plasmodium falciparum.
Other Identifiers: RSC Advances, 2014, 4, 26757-26770
Appears in Collections:Medicinal and Process Chemistry

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