title: An efficient lactamisation/N-acyliminium Pictet-Spengler domino strategy for the diasteroselective synthesis of polyhydroxylated quinoxalinone, β-carboline and quinazolinone derivatives.
abstract: A novel cascade strategy has been developed for the synthesis of polyhydroxylated tetrahydroindolo[1,2-a]pyrrolo[2,1-c]quinoxaline, tetrahydrodipyrrolo[1,2-a:2',1'-c]quinoxaline, hexahydro-1H-indolizino[8,7-b]indole, hexahydrobenzo[6,7]pyrrolo[1',2':1,2]azepino[3,4-b]indole, tetrahydrobenzo[4,5]imidazo[1,2-c]pyrrolo[1,2-a]quinazoline, and tetrahydropyrrolo[1,2-a]tetrazolo[1,5-c]quinazoline scaffolds. The key step is a lactamisation/Pictet-Spengler condensation of a bifunctional sugar-derived hydroxy-γ-lactone component with an appropriate bifunctional aromatic amine component. This modular approach features the in situ-generation of a cyclic N-acyliminium intermediate that allows the diastereoselective assembly of these diverse polycyclic systems efficiently under mild and operationally simple conditions.
authors.affiliation: Centre for Semiochemicals, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500 007, India. basireddy@iict.res.in.
authors.forename: B V
authors.initials: BV
authors.lastname: Subba Reddy
authors.affiliation: Centre for Semiochemicals, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500 007, India. basireddy@iict.res.in and Department of Chemistry, Yogi Vemana University, Kadapa, 516003, India.
authors.forename: B P
authors.initials: BP
authors.lastname: Reddy
authors.affiliation: Department of Chemistry, Yogi Vemana University, Kadapa, 516003, India.
authors.forename: P V G
authors.initials: PV
authors.lastname: Reddy
authors.affiliation: Laboratoire de Glycochimie, des Antimicrobiens et des Agroressources, UMR 7378 CNRS, 33 rue Saint-Leu, 80039 Amiens, France. aloysius.siriwardena@u-picardie.fr.
authors.forename: A
authors.initials: A
authors.lastname: Siriwardena