title: A new route for the synthesis of highly substituted 4-aminoquinoline drug like molecules via aza hetero-Diels-Alder reaction.
abstract: We have demonstrated for the first time the use of 2H-indazole as a diene partner in an aza hetero-Diels-Alder reaction leading to highly substituted 4-aminoquinolines via a heterocylic-heterocylic (H-H) strategy and have further developed a tandem one-pot method starting from 2-azidobenzaldehyde by the formation of 2C-N, 1N-N and 1C-C bonds. The key features of the present protocol are readily available starting materials, mild reaction conditions, being work-up free and having easy purification. This is the first time where the synthesis of 4-aminoquinoline drug like molecules has been achieved starting from simple starting materials in an atom economical manner.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Hyderabad, ODF-Estate, Yeddumailaram-502205, Medak, Telangana, Hyderabad, India. sharada@iith.ac.in.
authors.forename: Shinde
authors.initials: S
authors.lastname: Vidyacharan
authors.forename: A
authors.initials: A
authors.lastname: Sagar
authors.forename: Duddu S
authors.initials: DS
authors.lastname: Sharada
mesh_terms: D000634:Aminoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure
chemical_list: D000634:Aminoquinolines; C001920:4-aminoquinoline