title: A chemoselective Ugi-type reaction in water using TMSCN as a functional isonitrile equivalent: generation of heteroaromatic molecular diversity.
abstract: KF-mediated nucleophilic activation of TMSCN as a functional isonitrile equivalent establishes an efficient and chemoselective Ugi-type multicomponent reaction of a heterocyclic amidine and aldehyde with TMSCN in water. In this approach, the use of isocyanide is circumvented, known competing reactions are virtually eliminated, pure products are obtained by a non-chromatographic method, and therapeutically relevant and diverse N-fused 3-aminoimidazoles can be prepared from a wide variety of aldehydes and heterocyclic amidines. This reaction coupling with cascade cyclization provides various privileged tetracyclic heteroaromatic scaffolds.
authors.affiliation: Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), S. A. S. Nagar, Mohali - 160062, Punjab, India. skguchhait@niper.ac.in
authors.forename: Sankar Kumar
authors.initials: SK
authors.lastname: Guchhait
authors.forename: Vikas
authors.initials: V
authors.lastname: Chaudhary
authors.forename: Chetna
authors.initials: C
authors.lastname: Madaan
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D001550:Benzamidines / Q000737:chemistry*; D003486:Cyanides / Q000737:chemistry*; D003500:Cyclization; D005459:Fluorides / Q000737:chemistry*; D007093:Imidazoles / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009570:Nitriles; D017680:Potassium Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry*; D014867:Water
chemical_list: D000447:Aldehydes; D001550:Benzamidines; D003486:Cyanides; D007093:Imidazoles; D009570:Nitriles; D017680:Potassium Compounds; D014297:Trimethylsilyl Compounds; D014867:Water; C058010:trimethylsilyl cyanide; C033320:potassium fluoride; D005459:Fluorides