Synthesis and structure of novel 3,4‐annelated coumarin derivatives

Abstract

Condensation of 4‐chloro‐2‐oxo‐2H‐chromene‐3‐carbonitrile (1) with heteroarylamines 2a‐d in acetonitrile containing a catalytic amount of triethylamine followed by spontaneous intramolecular cyclization gave the novel coumarin derivatives 3a‐d, respectively. These compounds underwent acid hydrolysis giving the corresponding oxoderivatives 4a‐d. The structural assignments of the synthesized compounds were based on elemental, IR, 1H and 13C NMR analyses.

Synthesis and Antimicrobial Activity of New 4-Heteroarylamino Coumarin Derivatives Containing Nitrogen and Sulfur as Heteroatoms

“…Additionally, a recent QSAR study of the antimicrobial activity of some 3-nitrocoumarins has put forward some new arguments in this direction [ 19 ]. In connection with our previous work [ 20 , 21 , 22 , 23 , 24 ], in the present paper we report on the synthesis of novel 4-heteroarylamino-3-nitrocoumarin derivatives and the screening of their in vitro antimicrobial activity.…”

“…In continuation of our ongoing interest in synthesis of the new coumarin derivatives [ 20 , 21 , 22 , 23 , 24 ], and having in mind the above considerations, we have been prompted to synthesize new, possibly more potent, pharmacologically active compounds. We decided to combine the coumarinic system with the above named groups of compounds in hope that the resulting novel heterocycles would be biologically active.…”

Synthesis andin vitrobiological evaluation of 3, 4-annelated coumarin-pyrimido-pyrimidine systems

“…Previously, Govori et al (2002) synthesized few different 3,4-annelated coumarin systems including coumarin-pyrimido-pyrazole, coumarin-pyrimido-triazole, coumarin-pyrimido-pyridine, coumarin-pyrimido-benzothiazole, and coumarin-pyrimido-isoquinoline. Continuing our studies (Govori et al 1996;Daci-Ajvazi, Govori, and Omeragiq 2011;Deki c et al 2008) on the chemistry of 3,4-disubstituted coumarin and coumarin annelated in 3,4-positions, the following were prepared annelated coumarin-pyrimido-pyrimidine systems: 7-imino-8-mercapto-7H-5-oxa-7a,9,12-triaza-benzo[a]anthracen-6-one 2 and 8-hydroxy-7-imino-10-methyl-7H-5-oxa-7a,9,12-triaza-benzo[a]anthracen-6-one 3, starting from 4-chlorocoumarin-3-carbonitrile 1 (Govori et al 2002). The synthesized compounds were subjected to in vitro antibacterial activity.…”

A small library of 4-(alkylamino)-3-nitrocoumarin derivatives with potent antimicrobial activity against gastrointestinal pathogens

“…4 This is substantiated by the extensive use of coumarin compound-containing herbal remedies in the traditional medicine of many nations due to their broad spectrum of pharmacological activities, including antibacterial and antifungal effects. [9][10][11][12][13][14] A number of these compounds showed strong activity in reducing the microbial growth comparable or even better than the activity of standard antibiotics. 8 In connection with this, several arylamino-and (heteroarylamino)-3-nitrocoumarin derivatives were synthesized and their antimicrobial activity determined.…”