Synthesis of optically active-α-(imidazol-1-yl, purin-9-yl or uracil-1-yl) propanoic and succinic acid derivatives

Synthesis and Characterization of 6‐Carbamoyl‐1,2‐dihydropurines

“…Formimidate (4) was prepared in high yield from diaminomaleonitrile and triethyl orthoformate, according to a previously described procedure [6][7][8] . Having obtained the imidate (4) in good yield (94%) it was then treated with aryl or benzylamine in a 1:1 molar ratio in ethanol in the presence of a catalytic amount of anilinium chloride 8,9 . We thus attempted to cyclise the amidines 5a-b to obtain compounds of type 6a-b, in 78% yield by treatment with DBU (1, 8-diazabicyclo[5.4.0]undec-7-ene) in ethanol.…”

“…Since the discovery of acyclovir great research effort has been devoted to the synthesis of new acyclic nucleoside analogues as potential anti-herpes (HSV) and anti-human cytomegalovirus (HCMV) agents, 1 potent antiviral activities have been found for 'carboacyclic' nucleoside analogues such as 1, 1,2 and purine derivatives with simple 9-hydroxyalkyl substituents, such as 2 and 3, have biological activity [3][4][5][6][7][8] .…”

“…These have been found to be useful intermediates for the synthesis of new compounds 9-phenyl and 9-benzyl-1, 2-dihydropurine [15][16][17][18][19] . General procedure for the preparation of the 2- [6][7][8] (1.00 g) in dry ethanol (8 mL) was added DBU (9 drops). The mixture was stirred under an argon atmosphere at room temperature for 0.5-3 h. After this time, TLC showed that all the amidine had been consumed.…”

Utilities of Some Carbon Nucleophiles in Heterocyclic Synthesis

“…The preparation of O-alkylimidates 193 from -aminonitriles 192 and subsequent co-cyclization of such imidates with primary amines to afford 4-substituted 5-aminoimidazoles 194 (Scheme 61) previously has been documented in the literature [110][111][112][113][114][115].…”

Synthesis and Characterization of 9‐Phenyl‐9H‐purin‐6‐amines from 5‐Amino‐1‐phenyl‐1H‐imidazole‐4‐carbonitriles

“…Purines are a class of heterocyclic compounds which play an important role in many biological processes 1-5. The most important natural occurrence of purines is in the nucleotides and nucleic acids; compounds which perform some of the most crucial functions in fundamental metabolism. The chemotherapeutic uses of purines and purine analogues have prompted tremendous efforts towards their synthesis, both in academia and in the pharmaceutical industry [6][7][8][9] .…”