52066-00-9

Usage

Structure

Complex 3-dimensional structure with a benzimidazole ring fused with a triazine ring

Functional Groups

Amino Group: Provides basic properties
Carbonyl Group: Provides acidic properties

Family

Belongs to the s-triazine family

Applications

Medicinal Chemistry: Used as a building block for synthesizing various biologically active compounds
Anticancer Agents: Used in the development of anticancer agents
Antiviral Agents: Used in the development of antiviral agents

Utility

Valuable tool for the design and discovery of new pharmaceuticals due to its unique structure and reactivity.

Upstream product

• 102-09-0 bis(phenyl) carbonate 
• 5418-95-1 2-guanidinobenzimidazole 
• 1972-28-7 diethylazodicarboxylate 
• 105-58-8 Diethyl carbonate 
• 103-71-9 phenyl isocyanate 
• 95-54-5 1,2-diamino-benzene 

Relevant academic research and scientific papers

Microwave-assisted synthesis of s-triazino[2,1-b][1,3]benzoxazoles, s-triazino[2,1-b][1,3]benzothiazoles, and s-triazino[1,2-a]benzimidazoles

2-Amino-4-oxo-derivatives of s-triazino[2,1e][1,3]benzoxazoles, s-triazino[2,1,b][1,3]benzothiazoles, and s-triazino[1,2-a]benzimidazoles were synthesized by carbonylation of 2-benz-oxazolylguanidines, 2- benzothiazolylguanidines, and 2-benzimidazolylguanidines with phenyl isocyanate under microwave irradiation (180°C, 15 minutes). Using phenyl isothiocyanate instead of phenyl isocyanate under the same conditions led to the successful ring closure via thiocarbonylation of 2-benzoxazolylguanidines. However, the formation of 2-imino-4-phenylimino-s-triazino[2,1-b][1,3]benzothiazoles from 2-benzothiazolylguanidines was observed instead under microwave irradiation conditions. Georg Thieme Verlag Stuttgart.

Synthesis of 2-amino-s-triazino[1,2-a]benzimidazoles as potential antifolates from 2-guanidino- and 2-guanidino-5-methylbenzimidazoles

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

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