title: Synthesis of benzofuro[3,2-b]indoline amines via deamination-interrupted Fischer indolization and their unexpected reactivity towards nucleophiles.
abstract: We report the access to the benzofuro[3,2-b]indoline framework of phalarine from benzofuran-2-ones via the Fischer indolization reaction which was interrupted at the deamination step. Unexpectedly, allyl nucleophiles did not add to the aminal position of these benzofuro[3,2-b]indoline amines but to the adjacent ring junction center in the presence of trifluoroborane to deliver 3,3-disubstituted indolines containing a difluoroboron-containing six-membered ring with fluorescence properties.
authors.affiliation: Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Equipe Méthodologie, Synthèse et Molécules Thérapeutiques (MS&MT), Univ Paris Sud, CNRS, Université Paris-Saclay, 91405, Orsay, France. guillaume.vincent@u-psud.fr.
authors.forename: Terry
authors.initials: T
authors.lastname: Tomakinian
authors.affiliation: Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Equipe Méthodologie, Synthèse et Molécules Thérapeutiques (MS&MT), Univ Paris Sud, CNRS, Université Paris-Saclay, 91405, Orsay, France. guillaume.vincent@u-psud.fr.
authors.forename: Régis
authors.initials: R
authors.lastname: Guillot
authors.affiliation: Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Equipe Méthodologie, Synthèse et Molécules Thérapeutiques (MS&MT), Univ Paris Sud, CNRS, Université Paris-Saclay, 91405, Orsay, France. guillaume.vincent@u-psud.fr.
authors.forename: Cyrille
authors.initials: C
authors.lastname: Kouklovsky
authors.affiliation: Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Equipe Méthodologie, Synthèse et Molécules Thérapeutiques (MS&MT), Univ Paris Sud, CNRS, Université Paris-Saclay, 91405, Orsay, France. guillaume.vincent@u-psud.fr.
authors.forename: Guillaume
authors.initials: G
authors.lastname: Vincent
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D001572:Benzofurans / Q000138:chemical synthesis / Q000737:chemistry*; D001896:Boron Compounds / Q000138:chemical synthesis / Q000737:chemistry; D003641:Deamination; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D054879:Halogenation; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000470:Alkaloids; D000588:Amines; D001572:Benzofurans; D001896:Boron Compounds; D005456:Fluorescent Dyes; D007211:Indoles; C552076:phalarine; C057812:indoline