A facile and rapid one-step synthesis of 8-substituted xanthine derivatives via tandem ring closure at room temperature

• Published in: Tetrahedron 2012-05, Vol.68 (20), p.3822-3827
• Main Authors: Bandyopadhyay, Prabal, Agrawal, Sumit K., Sathe, Manisha, Sharma, Pratibha, Kaushik, M.P.
• Format: Article
• Language: English
• Subjects: Adenosine receptor antagonist; AIBN; Analytical, structural and metabolic biochemistry; Biological and medical sciences; Chemistry; Chromatography; Derivatives; Exact sciences and technology; Free radicals chemistry; Fundamental and applied biological sciences. Psychology; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Medical sciences; N-Bromo succinimide (NBS); Neuropharmacology; Neurotransmitters. Neurotransmission. Receptors; Nucleic acids; Nucleic bases, nucleotides; Organic chemistry; Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems; Pharmacology. Drug treatments; Preparations and properties; Radical chain reaction; Radicals; Reactivity and mechanisms; Solvents; Succinimides; Synthesis; Tetrahedrons; Xanthine; Xanthines
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2012.03.050

N-Bromo succinimide (NBS) was found to be an efficient and regioselective reagent in combination with AIBN for an unprecedented, facile and rapid one-step synthesis of 8-substituted xanthine derivatives at room temperature. The inexpensive, nontoxic and readily available NBS efficiently promoted the condensation of several aryl/cycloaryl/heteroaryl aldehydes with 5,6-diamino-1,3-dimethyluracils in presence of catalytic amount of AIBN in a single step via radical chain reaction. The notable advantages of this protocol were short reaction time, milder reaction conditions, simple work-up procedure, no requirement for chromatographic separation, use of non-hazardous reagent/solvent and applicable to a variety of substrates. [Display omitted]