Synthesis, Reactions and Evaluation of the Antimicrobial Activity of Some 4-(p-Halophenyl)-4H-naphthopyran, Pyranopyrimidine and Pyranotriazolopyrimidine Derivatives
Open Access
- 12 July 2012
- journal article
- research article
- Published by MDPI AG in Pharmaceuticals
- Vol. 5 (7), 745-757
- https://doi.org/10.3390/ph5070745
Abstract
A series of naphthopyran derivatives 3a–f were prepared. Reaction of 2-amino-4-(p-chlorophenyl)-7-methoxy-4H-naphtho[2,1-b]pyran-3-carbonitrile (3b) with Ac2O afforded two products, 2-acetylamino-7-methoxy-4-(p-chlorophenyl)-4H-naphtho-[2,1-b]pyran-3-carbonitrile (4) and 10,11-dihydro-3-methoxy-9-methyl-12-(p-chloro-phenyl)-12H-naphtho[2,1-b]pyran[2,3-d]pyrimidine-11-one (5) and treatment of 3b with benzoyl chloride gave the pyranopyrimidin-11-one derivative 6. While treatment of 3b with formamide afforded 11-amino-3-methoxy-12-(p-chlorophenyl)-12H-naphtho[2,1-b]pyrano[2,3-d]pyrimidine (7). Reaction of 3b with triethyl orthoformate gave the corresponding 2-ethoxymethyleneamino-7-methoxy-4-(p-chlorophenyl)-4H-naphtho-[2,1-b]pyran-3-carbonitrile (8). Hydrazinolysis of 8 in EtOH at room temperature yielded 10-amino-10,11-dihydro-11-imino-3-methoxy-12-(p-chlorophenyl)-12H-naphtho[2,1-b]pyrano-[2,3-d]pyrimidine (9), while aminolysis of 8 with methylamine or dimethylamine gave the corresponding pyranopyrimidine and N,N-dimethylaminomethylene derivatives 10 and 11. Condensation of 9 with some carboxylic acid derivatives afforded triazolopyrimidine derivatives 12–16, while reaction of 9 with benzaldehyde gave 10-benzalamino-10,11-dihydro-11-imino-3-methoxy-12-(p-chlorophenyl)12H-naphtho[2,1-b]pyrano[2,3-d]pyrimidine (17). The structures of the newly synthesized compounds were confirmed by spectral data. The synthesized compounds were also screened for their antimicrobial activity.This publication has 20 references indexed in Scilit:
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