Synthesis and anti-bacterial activities of novel 5-isonicotinoyl-1,2,3,4-tetrahydropyrimidines and bis-(5-isonicotinoyl-1,2,3,4-tetrahydropyrimidines)

Abstract

Novel 5-isonicotinoyl-1,2,3,4-tetrahydropyrimidines 4a-i have been synthesized in good yields by the reaction of enaminones 3a-c, primary amines and formaldehyde. 4a-i have been screened for their antibacterial properties. Enaminones 3a-c have also been reacted with diamines and formaldehyde to give hitherto unreported bis-tetrahydropyrimidines 5a-l in good yields. The structures of 4a-i and 5a-l have been established with the help of spectral and analytical data.

2-Amino-4,5-dihydrothiophene-3-carbonitriles: A New Synthesis, Quantum Chemical Studies, and Mannich-Type Reactions Leading to New Hexahydrothieno[2,3-d]pyrimidines

“…It should be noted that ADHTs 6 play here an unusual role of 1,3-dinucleophilic β-enaminonitrile species. In general, the Mannich-type reactions of β-enaminocarbonyls and related enamines with HCHO and primary amines leading to tetrahydropyrimidines are well known; − however, as far as we know, no cyclic enaminonitriles were reported as substrates in the Mannich reaction prior to our studies.…”

Catalyst-free multicomponent synthesis of novel adamantyl-containing tetrahydropyrimidine carboxylates

“…The protons of adamantyl group appeared as three distinct multiplets in ranges 1.54-1.73, 1.75-1.85, and 2.05-2.09 ppm. In the 13 C NMR spectra, Scheme 3 Reaction of dimethyl acetylenedicaboxylate (1)/methylpropiolate (6) with adamantanamine (4) the signals for the three types of adamantyl group carbon atoms appeared in ranges of 29.5-29.7, 35.5-36.6, 39.6-41.3 and 41.0-41.7 ppm. The mass spectral data of the products supported the proposed structures well.…”

“…Keeping in mind the insecticidal and pesticidal properties of 1,2,3,4-tetrahydropyrimidine derivatives with nitro group in position 5 (Nitro-THP-1) [1,2], we have developed synthetic strategies for novel 5-benzoyl-1,2,3,4-tetrahydropyrimidines (Benzoyl-THP-2) [3] and 5-isonicotinoyl-1,2,3,4-tetrahydro pyrimidines (Isonicotinoyl-THP-3) [4] having benzoyl and isonicotinoyl groups respectively in position 5. Also, our group has reported the synthesis of novel bis-tetrahydropyri midines (Benzoyl-THP-4) [5].…”