Novel synthesis of biologically active indolo [3,2-C] isoquinoline derivatives

• Main Author: Prabhuodeyara M. Veeresha Sharma
• Format: Article
• Language: English
• Published: Elsevier 2017-07-01
• Series: Arabian Journal of Chemistry
• Subjects: Indole-2-carboxylates; Thiones; Indolo [3,2-C] isoquinolin-2′-yl sulfanyl methylene benzimidazole
• Online Access: http://www.sciencedirect.com/science/article/pii/S1878535214001440

Indole-2-carboxylates are refluxed with hydrazine hydrate to form 5-substituted-3-phenylindole-2-carboxyhydrazides. These are again converted to corresponding indole-2-carboxyazides. Azides are further converted into carbamates and finally these carbamates are cyclized to form the respective substituted 6H, 11H-indolo [3,2-C] isoquinolin-2-ones (1a–c). These (1a–c) were reacted with phosphorus pentasulfide in refluxing pyridine to yield the respective thiones (2a–c). These thiones (2a–c) on reaction with chloroacetic acid and sodium acetate in acetic acid under refluxing temperature for 5 h yielded isoquinoline-thioacetic acids (3a–c). Compounds (3a–c) on reaction with orthopheneylene diamine dihydrochloride in ethylene glycol at refluxing temperature yielded substituted indolo [3,2-C] isoquinolin-2′-yl sulfanyl methylene benzimidazoles (4a–c).