Dimethylformamide dimethyl acetal as a building block in heterocyclic synthesis

Abstract

This review focuses on the use of dimethylformamide dimethyl acetal in the preparation of heterocyclic compounds via formylation of active methylene groups, methyl groups to give enamines, and formylation of amino groups to give amidines. These compounds are found to be useful intermediates in the formation and modification of heterocyclic compounds.

Synthesis of a Novel Tri‐enaminone as Building Block for Polyaza‐heterocycles

“…IR spectra were recorded in KBr using PyUnicam SP-1000 Spectrometer. 1 HNMR spectra were recorded using CDCl 3 and DMSO-d 6 solutions using a Varian Em-300 MHz Spectrometer, and chemical shifts are reported in ppm relative to that of TMS, which was used as an internal standard. Mass spectra were recorded using a AEI MS 30 mass spectrometer operating at 70 eV.…”

“…1 H NMR spectrum of 3 exhibits four singlet signals at δ 2.38, 2.45, 2.59, and 2.66 assignable to the 5-methyl and the three acetyl groups, in addition to the signals expected for the aromatic protons (see Experimental).…”

Synthesis of Novel Bis-enaminones by KHSO4-assisted Facile Michael Addition-elimination Reaction of 3-(dimethylamino)-1-phenylprop-2-en-1-ones with Diamines in Water

“…The IR spectra were recorded on a Perkin-Elmer 983 spectrometer. 1 H NMR and 13 C NMR spectra were recorded on Bruker ACF-300 spectrometer. The chemical shifts (δ ppm) and the coupling constants (Hz) are reported in the standard fashion with reference to TMS as internal reference.…”

“…Formylated products obtained by reacting active proton compounds with dimethylformamide-dimethylacetal (DMF-DMA) have proved to be very useful intermediates in the formation and modification of heterocyclic compounds [1]. Keeping in view the synthetic potential of 3-(dimethylamino)-1-phenylprop-2-en-1-ones (formylated acetophenones) [2][3][4][5][6][7][8][9][10][11][12], we recently reported an efficient method for the formylation of active proton compounds [13].…”

The Behavior of 3-Anilinoenone and N-Phenyl Cinnamamide toward Carbon Nucleophiles: Spectroscopy and X-Ray Studies Reveal Interesting New Synthesis Routes to Nicotinonitriles and Tetrahydropyridine-3- Carbonitrile

“…Due to their biological activities and pharmacological properties, pyridines and pyridones represent an important class of compounds that have been developed using functionally substituted enaminones [16][17][18][19][20][21][22]. In continuation of our interest in the synthesis of functionally substituted heteroaromatic compounds such as pyridines and pyridones, utilizing enaminones as starting materials [22][23][24][25][26][27][28][29][30][31][32][33], we report here the behavior of 3-anilinoenone and N-phenyl cinnamamide derivative toward malononitrile in the synthesis of pyridine derivatives.…”