Synthesis and biological activity of hexahydropyrimidine and carbamate derivatives
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Date
2017-08
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G.B. Pant University of Agriculture and Technology, Pantnagar - 263145 (Uttarakhand)
Abstract
Hexahydropyrimidine derivatives have been synthesized by the reaction of different 1,3dicarbonyl compounds, aniline derivatives and formaldehyde catalysed by Calcium chloride dehydrate under solvent free conditions at room temperature. calcium chloride dihydrade offers simple, efficient and economical method. The compounds synthesized were 5-acetyl-1,3-diphenylhexahydropyrimidine-5-ethyl ester, 5-acetyl-1,3-bis(2-chlorophenyl)-hexahydropyrimidine-5-ethyl ester, 5-acetyl-1,3bis(4-fluorophenyl)-hexahydropyrimidine-5-ethyl ester, 5-acetyl-1,3-bis(2chlorophenyl)-hexahydropyrimidine-5-methyl ester, 5-acetyl-1,3-bis (2,4-dimethylphenyl) hexahydropyrimidine-5-ethyl ester, 5-acetyl-1,3-bis(4-hydroxyphenyl)-hexahydropyrimidine-5ethyl ester, 5-acetyl-1,3-diphenyl-hexahydropyrimidine-5-methyl ester, 5-acetyl-1,3-bis(4fluorophenyl)-hexahydropyrimidine-5-methyl ester, 5-acetyl-1,3-bis(2,4-dimethylphenyl)hexahydropyrimidine-5-methyl ester, 5-acetyl-1,3-bis(4-hydroxyphenyl)-hexahydropyrimidine-5methyl ester, 9,9-dimethyl-1,3-diphenyl-1,3-diazaspiro (5.5) undecane-7,11-dione. All the compounds were formed in good to excellent yield. Carbamates have been synthesized by the reaction of substituted benzeldehyde, acetophenone derivatives, malononitrile and diethyl-carbonate using organocatalyst proline under solvent free conditions at 400C. The compounds synthesized were ethyl-N-(2,6 dicyano-3,5-diphenylphenyl) carbamate, ethyl-N-[2,6- dicyano-3-(4fulorophenyl)-5 phenyl phenyl] carbamate, ethyl-N-[2,6 dicyano-3-(4-hydroxyphenyl)-5-phenyl phenyl] carbamate, ethyl-N-[2,6- dicyano-3-(4-methoxyphenyl)-5-phenyl phenyl] carbamate, ethyl-N-[2,6- dicyano-3-(dimethyl amino phenyl)-5- phenyl phenyl] carbamate, ethyl-N-[2,6dicyano-3-(2-nitrophenyl)-5-phenyl phenyl] carbamate, ethyl-N-[2,6- dicyano-3-(4-nitrophenyl)-5phenylphenyl] carbamate, ethyl-N-[3-(4-chlorophenyl)-2,6dicyano-5-phenylphenyl] carbamate, ethyl-N-[2,6-dicyano-3-(4-hydroxyphenyl)-5-phenylphenyl] carbamate, ethyl-N-[2,6- dicyano-3(2-hydroxyphenyl)-5-phenylphenyl] carbamate, ethyl-N-[3-(2-chlorophenyl)-2,6-dicyano-5phenylphenyl] carbamate. Most of the compounds were formed in good to excellent yield. The present work clearly establishes the efficacy of catalysts as an inexpensive, non-toxic, easily available and environmentally benign for the synthesis. All the compounds were tested for seed germination inhibition activity. Most of derivatives of hexahydropyrimidine were found to exhibit significantly lower activity than standard butachlor. While all the carbamate derivatives were found to exhibit very good seed germination inhibition activity. Two carbamate compounds ethylN-(2,6-dicyano-3,5-diphenylphenyl) carbamate, ethyl-N-[2,6-dicyano-3-(dimethylaminophenyl)-5phenylphenyl] were found to exhibit activity at par with standard butachlor. Thus synthesized carbamates may be explored for the development of potential herbicides.
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