title: 1,3-Aminoalkoxylation and phenolation/dimerization of maleimide-derived Morita-Baylis-Hillman adduct of isatin via domino azidation-Michael addition/aza-Diels-Alder reaction.
abstract: NaN3-ROH/ArOH has been found to be an efficient reagent for 1,3-amino alkoxylation and 1,3-amino phenolation of a maleimide-derived MBH adduct of isatin via domino azidation-Michael addition. Following this protocol, with NaN3-formalin, a one-pot synthesis of 3-spiro-1,2-dihydropyrrolooxazine-5,7-dione-oxindole has been achieved. In an aprotic medium, the reaction underwent an unusual amino dimerization via an aza-Diels-Alder reaction of a common allylic imine intermediate.
authors.affiliation: Council of Scientific and Industrial Research (CSIR)-Central Leather Research Institute (CLRI), Organic Chemistry Division , Adyar, Chennai-600020, India.
authors.forename: Rajarethinam
authors.initials: R
authors.lastname: Solaiselvi
authors.forename: Ponnusamy
authors.initials: P
authors.lastname: Shanmugam
mesh_terms: D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D061565:Cycloaddition Reaction; D003959:Diamines / Q000737:chemistry*; D019281:Dimerization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007510:Isatin / Q000737:chemistry*; D008301:Maleimides / Q000737:chemistry*; D015394:Molecular Structure; D010078:Oxazines / Q000138:chemical synthesis* / Q000737:chemistry; D000078183:Oxindoles; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C587702:3-spiro-1,2-dihydropyrrolooxazine-5,7-dione-oxindole; D001386:Azides; D003959:Diamines; D007211:Indoles; D008301:Maleimides; D010078:Oxazines; D000078183:Oxindoles; D013141:Spiro Compounds; C043592:maleimide; D007510:Isatin