title: [4 + 3] Cycloadditions with Bromo-Substituted Morita-Baylis-Hillman Adducts of Isatins and N-(ortho-Chloromethyl)aryl Amides.
abstract: Efficient construction of a challenging aza-spirocycloheptane oxindole scaffold is reported through an unprecedented [4 + 3] cycloaddition reaction with bromo-substituted Morita-Baylis-Hillman adducts of isatins and N-(ortho-chloromethyl)aryl amides. Both reactive intermediates, the allylic phosphonium ylides and aza-o-quinone methides, were in situ generated, chemoselectively facilitated by a Lewis base and Brønsted base, respectively.
authors.affiliation: Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, West China Hospital, Sichuan University , Chengdu 610041, China.
authors.forename: Gu
authors.initials: G
authors.lastname: Zhan
authors.affiliation: Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, West China Hospital, Sichuan University , Chengdu 610041, China.
authors.forename: Ming-Lin
authors.initials: ML
authors.lastname: Shi
authors.affiliation: Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, West China Hospital, Sichuan University , Chengdu 610041, China.
authors.forename: Qing
authors.initials: Q
authors.lastname: He
authors.affiliation: Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, West China Hospital, Sichuan University , Chengdu 610041, China.
authors.forename: Wei
authors.initials: W
authors.lastname: Du
authors.affiliation: Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, West China Hospital, Sichuan University , Chengdu 610041, China.|College of Pharmacy, Third Military Medical University , Shapingba, Chongqing 400038, China.
authors.forename: Ying-Chun
authors.initials: YC
authors.lastname: Chen
mesh_terms: D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D061565:Cycloaddition Reaction; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry; D007510:Isatin / Q000737:chemistry*; D058115:Lewis Bases / Q000737:chemistry; D015394:Molecular Structure; D000078183:Oxindoles; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000577:Amides; D006576:Heterocyclic Compounds, 4 or More Rings; D006843:Hydrocarbons, Chlorinated; D007211:Indoles; D058115:Lewis Bases; D000078183:Oxindoles; D013141:Spiro Compounds; C022960:2-oxindole; D007510:Isatin