One-pot, four-component synthesis of fully substituted 1,3,4-oxadiazole derivatives from N-isocyaniminotriphenylphosphorane (Ph3PNNC), a primary amine, a carboxylic acid and cinnamaldehyde
Journal Title: Iranian Chemical Communication - Year 2016, Vol 4, Issue 2
Abstract
The imine intermediate generated by the addition of primary amine to the cinnamaldehyde is trapped by the N-isocyaniminotriphenylphosphorane (Ph3PNNC) and a carboxylic acid, and leads to the formation of the corresponding iminophosphorane intermediate. The 1,3,4-oxadiazole derivatives are formed via intramolecular aza-Wittig reaction of the iminophosphorane intermediate. The reactions were completed under neutral conditions at room temperature. The fully substituted 1,3,4-oxadiazole derivatives were produced in high yields. The method offers a mild, simple, and efficient route for the preparation of fully substituted 1,3,4-oxadiazols. The structures of the products were deduced from their IR, 1H NMR, 13C NMR spectra, and mass spectrometry.
Authors and Affiliations
Ali Ramazani, Fatemeh Kalantari
Keywords
Related Articles
- EP ID EP259285
- DOI -
- Views 109
- Downloads 0
A green and eco-friendly method for the synthesis of xanthene derivatives using cellulose sulfuric acid under solvent-free conditions
A green and convenient method for the synthesis of 14-aryl-14H-dibenzo[a,i]xanthene-8,13-diones and spiro[dibenzo[a,i]-xanthene-14,3'-indoline]-2',8,13-triones in the presence of a catalytic amount of cellulose sulfuric...
Quantitative structure-activity relationship (QSAR) study of CCR2b receptor inhibitors using SW-MLR and GA-MLR approaches
In this paper, the quantitative structure activity-relationship (QSAR) of the CCR2b receptor inhibitors was scrutinized. Firstly, the molecular descriptors were calculated using the Dragon package. Then, the stepwise mul...
Microwave assisted green synthesis of α, ά- bis (substituted- benzylidene) alkanones
Microwave assisted green synthesis of α, ά- bis (substituted- benzylidene) alkanones by the crossed- aldol condensation reaction of substituted aryl aldehydes with ketones in the presence of catalytic amount of NbCl5 in...
Synthesis, spectroscopic (NMR and FT-IR) and theoretical (HF and DFT) investigation of dimethyl (Z)-2-[(2-methyl-5-oxo-1-cyclopentyl)oxy]-2-butendioate
Dimethyl (z)-2-[(2-methyl-5-oxo-1-cyclopentyl)oxy]-2-butenedioate has been synthesized using one-pot three component reaction between N-isocyaniminotriphenylphosphorane (Ph3PNNC), 3-methylcyclopentene-1,2-dione and dimet...
Synthesis of neopentyl glycol and ethylene glycol esters by fatty acids in the presence of acidic ion exchange resin catalyst
A most effective and less energy demanding method of producing fatty esters, diol esters, by esterifying fatty acids, with neopentyl and ethylenglycol alcohols in the presence of an acidic ion exchange resin catalyst(pol...