title: Facile synthesis of spiro[indoline-3,3'-pyrrolo[1,2-a]quinolines] and spiro[indoline-3,1'-pyrrolo[2,1-a]isoquinolines] via 1,3-dipolar cycloaddition reactions of heteroaromatic ammonium salts with 3-phenacylideneoxindoles.
abstract: A series of complex spiro[indoline-3,3'-pyrrolo[1,2-a]quinolines] were efficiently synthesized by 1,3-dipolar cycloaddition reactions of N-phenacylquinolinium bromides with 3-phenacylideneoxindoles in ethanol with triethylamine as base. Under similar conditions the 1,3-cycloadditions of N-phenacylisoquinolinium and N-phenacyl-1,10-phenanthrolinium bromides with 3-phenacylideneoxindoles resulted in the corresponding spiro[indoline-3,1'-pyrrolo[2,1-a]isoquinoline] and spiro[benzo[h]pyrrolo[1,2-a]quinoline-3,3'-indoline] derivatives in good yields. The characterization data of spiro compounds and single crystal determination indicated that this 1,3-cycloaddition reaction is a regioselective and diastereoselective reaction and all prepared spiro compounds exist in the thermodynamically stable trans isomer.
authors.affiliation: College of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, China.
authors.forename: Lei
authors.initials: L
authors.lastname: Wu
authors.forename: Jing
authors.initials: J
authors.lastname: Sun
authors.forename: Chao-Guo
authors.initials: CG
authors.lastname: Yan
mesh_terms: D061565:Cycloaddition Reaction; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D000078183:Oxindoles; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D012492:Salts / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007211:Indoles; D000078183:Oxindoles; D011758:Pyrroles; D000644:Quaternary Ammonium Compounds; D011804:Quinolines; D012492:Salts; D013141:Spiro Compounds; C022960:2-oxindole