Efficient novel synthesis of pyrano[3, 2-a]- and pyrazolo[4, 3-a]-acridines. Issue 3 (1st February 2017)

• Record Type: Journal Article
• Authors: Satheeshkumar, Rajendran; Kaminsky, Werner; Rajendra Prasad, Karnam Jayarampillai
• Is Part Of: Synthetic communications. Volume 47:Issue 3(2017)
• Page Start: 245
• Page End: 255
• Publication Date: 2017-02-01
• Subjects: 7-Chloro-9-aryl-2, 3-dihydroacridin-4(1H)-one -- 7-chloro-4-hydroxy-9-aryl-1, 2-dihydroacridin-3-carbaldehyde -- multicomponent reaction -- pyrano[3, 2-a]acridines -- pyrazolo[4, 3-a] acridines; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2016.1262038
• Languages: English
• ISSNs: 0039-7911

Abstract

ABSTRACT: The synthesis of pyrano[3, 2- a ]acridines is presented, where 7-chloro-9-phenyl-2, 3-dihydroacridin-4( 1H )-one reacts with arylaldehydes and malononitrile in the presence of piperidine in ethanol, giving with high yield via a multicomponent method. Also a new synthesis of pyrazolo[4, 3- a ]acridines is reported, where 7-chloro-9-aryl-2, 3-dihydroacridin-4( 1H )-one on Claisen condensation with ethylformate followed by hydrazine hydrate treatment through the intermediate 7-chloro-4-hydroxy-9-aryl-1, 2-dihydroacridin-3-carbaldehyde. The structures of newly synthesized compounds were deduced by spectroscopic techniques, elemental analysis, and single-crystal x-ray diffraction. GRAPHICAL ABSTRACT: