title: A one-pot azido reductive tandem mono-N-alkylation employing dialkylboron triflates: online ESI-MS mechanistic investigation.
abstract: An efficient one-pot reductive tandem mono-N-alkylation of both aromatic and aliphatic azides using dialkylboron triflates as alkylating agents has been examined under standardized reaction conditions. This methodology after optimization has been employed toward the syntheses of various secondary alkyl as well as aryl amines, including the synthesis of N10-butylated pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones via in situ azido reductive-cyclization process. This protocol is particularly attractive to provide an environmentally benign and practical method for mono-N-alkylation from organic azides without the use of toxic catalysts or corrosive alkylating agents. In addition, the mechanistic aspects have been investigated and the intermediates associated with this selective transformation have been intercepted and characterized by online monitoring of the reaction by ESI-MS/MS.
authors.affiliation: National Institute of Pharmaceutical Education and Research (NIPER), Hyderabad-500 037, India.
authors.forename: Nagula
authors.initials: N
authors.lastname: Shankaraiah
authors.forename: Nagula
authors.initials: N
authors.lastname: Markandeya
authors.forename: Vunnam
authors.initials: V
authors.lastname: Srinivasulu
authors.forename: Kokkonda
authors.initials: K
authors.lastname: Sreekanth
authors.forename: Ch Sanjeeva
authors.initials: ChS
authors.lastname: Reddy
authors.forename: Leonardo S
authors.initials: LS
authors.lastname: Santos
authors.forename: Ahmed
authors.initials: A
authors.lastname: Kamal
mesh_terms: D000478:Alkylation; D001386:Azides / Q000737:chemistry*; D001895:Boron / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D053719:Tandem Mass Spectrometry
chemical_list: D001386:Azides; D008698:Mesylates; D001895:Boron