52066-00-9Relevant articles and documents
Synthesis of 2-amino-s-triazino[1,2-a]benzimidazoles as potential antifolates from 2-guanidino- and 2-guanidino-5-methylbenzimidazoles
Dolzhenko, Anton V.,Chui, Wai-Keung
, p. 95 - 100 (2007/10/03)
The syntheses of 2-amino-s-triazino[1,2-a]benzimidazoles from 2-guanidinobenzimidazoles were successfully carried out by a ring annelation reaction. The regiochemistry of the ring closure of 5-methyl-2- guanidinobenzimidazole with diethyl azodicarboxylate, aldehydes, acetone, diethyl ethoxymethylene-malonate and orthoesters, leading to the formation of s-triazine ring was studied. High regioselectivity was not observed in any of these reactions. However, the synthesis of s-triazino[1,2-a]benzimidazole system was found to be more regioselective than its 3,4-dihydro analogue. NOESY experiment indicated that the compound, 2-amino-4,4-dimethyl-3,4-dihydro-s- triazino[1,2-a]benzimidazole existed predominantly as the 3,4-dihydro tautomer in dimethyl sulfoxide. It was found to inhibit bovine dihydrofolate reductase with IC50 10.9 μM.
Reaction of Biguanides and Related Compounds. XV. Cyclizations of Arylbiguanides and 2-Guanidinobenzimidazole with Bifunctional Unsaturated Dicarboxylates to s-Triazines and Imidazolines
Furukawa, Mitsuru,Kawanabe, Kimimasa,Yoshimi, Atsuko,Okawara, Tadashi,Noguchi, Yoshihide
, p. 2473 - 2479 (2007/10/02)
Arylbiguanide (1) and 2-guanidinobenzimidazole (2) were reacted with diethyl azodicarboxylate (3) to give dihydro-s-triazine (6) and dihydrobenzimidazol-s-triazine (9), respectively.The reaction of 1 and 2 with dimethyl acetylenedicarboxylate (4) in alcohol provided the corresponding imidazolinylideneacetylguanidines (10 and 12), which were converted to alkyl imidazolidinylideneacetates (11 and 13) by alcoholysis.The compounds 10 and 12 underwent acid-catalyzed ring conversion to pyrimidine compounds (15 and 16).Keywords - arylbiguanide; guanidinobenzimidazole; diethyl azodicarboxylate; dimethyl acetylenedicarboxylate; s-triazine; imidazoline; cyclization; ring conversion