Base-Promoted Cyclocondensation of (1E,4E)-1,5-Diarylpenta-1,4-dien-3-ones with Guanidine Hydrochloride: Facile Synthesis of E-2-Amino-4-Aryl-6-(2-Arylethenyl)Pyrimidines

Submit Manuscript | http://medcraveonline.com classes of pyrimidines. The pharmaceutical importance of these compounds lies on the fact that they can be effectively used as analgesics, anti-inflammatory, anticonvulsant, insecticidal, herbicidal, antitubercular, anticancer and antidiabetic agents [4-6]. Also, the pyrimidine and aminopyrimidine structures are frequently-occurring motifs in commercially available drugs such as anti-atherosclerotic aronixil [7], anti-anxiolytic buspirone [8], and other medicinally relevant compounds [9,10]. Symmetrical (1E,4E)-1,5-diarylpenta-1,4-dien-3-ones (1) and their unsymmetrical analogues (2), which could be constructed easily, also possess structural features similar to α,α’-bis(arylmethylene) cycloalkanones previously utilized by us for studying their reaction with thiourea and guanidine hydrochloride [11,12]. It is evident from the literature that the reaction of (1E,4E)-1,5diarylpenta-1,4-dien-3-ones (1 and 2) with guanidine has not been studied so far, although there are reports of cyclocondensation of varieties of α,β-unsaturated ketones with guanidine [13,14]. In this paper, we report a facile synthesis of E-2-amino-4-aryl-6-(2arylethenyl) pyrimidines by base-promoted cyclocondensation of various (1E,4E)-1,5-diarylpenta-1,4-dien-3-ones with guanidine hydrochloride.