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One-pot synthesis of dispiro[oxindole-3,3′-pyrrolidines] by three-component [3+2] cycloadditions of in situ-generated azomethine ylides with 3-benzylidene-2,3-dihydro-1H-indol-2-ones

Matloubia Moghaddam, F ; Sharif University of Technology | 2013

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  1. Type of Document: Article
  2. DOI: 10.1002/hlca.201200602
  3. Publisher: 2013
  4. Abstract:
  5. An efficient one-pot, three-component synthesis of novel dispiro[oxindole-3,3′-pyrrolidines] by 1,3-dipolar cycloaddition of azomethine ylides, in situ generated by reaction of 1,2-diones with sarcosine and subsequent decarboxylation, with a series of (E)-3-benzylidene-2,3-dihydro- 1H-indol-2-ones is reported. Molecular complexity is generated in only one synthetic step. All reactions proceed with excellent regioselectivity and in good-to-excellent yields. The workup is easy, the reaction times are short, and no catalyst is required. © 2013 Verlag Helvetica Chimica Acta AG, Zürich
  6. Keywords:
  7. Azomethine ylides ; Cycloadditions ; Dispiropyrrolidine ; Multicomponent reaction ; Multi-component reactions ; Spiro-oxindole ; Carboxylation ; Cycloaddition ; Synthesis (chemical) ; 1'' ethyl 1' methyl 4' (4 methylphenyl) 2h dispiro(acenaphthylene 1,2' pyrrolidine 3',3'' indole) 2,2''(1''h) dione ; 1'' ethyl 1' methyl 4' (4 methylphenyl)dispiro(indene 2,2' pyrrolidine 3',3'' indole) 1,2'',3(1''h) trione ; 1'' ethyl 1' methyl 4' phenyl 2h dispiro(acenaphthylene 1,2' pyrrolidine 3',3'' indole) 2,2''(1''h) dione ; 1'' ethyl 1' methyl 4' phenyldispiro(indene 2,2' pyrrolidine 3',3'' indole) 1,2'',3(1''h) trione ; 1'' ethyl 4' (4 methoxyphenyl) 1' methyldispiro(indene 2,2' pyrrolidine 3',3'' indole) 1,2'',3(1''h) trione ; 1'' ethyl 4' (furan 2 yl) 1' methyl 2h dispiro(acenaphthylene 1,2' pyrrolidine 3',3'' indole) 2,2''(1''h) dione ; 1',1'' dimethyl 4' (3 nitrophenyl) 2h dispiro(acenaphthylene 1,2' pyrrolidine 3',3'' indole) 2,2''(1''h) dione ; 1',1'' dimethyl 4' (3 nitrophenyl)dispiro(indene 2,2' pyrrolidine 3',3'' indole) 1,2'',3(1''h) trione ; 1',1'' dimethyl 4' (4 methylphenyl) 2h dispiro(acenaphthylene 1,2' pyrrolidine 3',3'' indole) 2,2''(1''h) dione ; 1',1'' dimethyl 4' (4 methylphenyl)dispiro(indene 2,2' pyrrolidine 3',3'' indole) 1,2'',3(1''h) trione ; 1',1'' dimethyl 4' phenyl 2h dispiro(acenaphthylene 1,2' pyrrolidine 3',3'' indole) 2,2''(1''h) dione ; 1',1'' dimethyl 4' phenyldispiro(indene 2,2' pyrrolidine 3',3'' indole) 1,2'',3(1''h) trione ; 4' (4 chlorophenyl) 1'' ethyl 1' methyldispiro(indene 2,2' pyrrolidine 3',3'' indole) 1,2'',3(1''h) trione ; 4' (4 chlorophenyl) 1',1'' dimethyl 2h dispiro(acenaphthylene 1,2' pyrrolidine 3',3'' indole) 2,2''(1''h) dione ; 4' (4 chlorophenyl) 1',1'' dimethyldispiro(indene 2,2' pyrrolidine 3',3'' indole) 1,2'',3(1''h) trione ; 4' (4 methoxyphenyl) 1',1'' dimethyl 2h dispiro(acenaphthylene 1,2' pyrrolidine 3',3'' indole) 2,2''(1''h) dione ; 4' (4 methoxyphenyl) 1',1'' dimethyldispiro(indene 2,2' pyrrolidine 3',3'' indole) 1,2'',3(1''h) trione ; 4' (furan 2 yl) 1' methyl 1'' phenyldispiro(indene 2,2' pyrrolidine 3',3'' indole) 1,2'',3(1''h) trione ; Azomethine ylide ; Indole derivative ; Pyrrolidine derivative ; Unclassified drug ; Carbon nuclear magnetic resonance ; Column chromatography ; Controlled study ; Crystal structure ; Decarboxylation ; Drug synthesis ; Isomer ; One pot synthesis ; Priority journal ; Reaction time ; Stereochemistry
  8. Source: Helvetica Chimica Acta ; Volume 96, Issue 11 , 2013 , Pages 2103-2114 ; 0018019X (ISSN)
  9. URL: http://onlinelibrary.wiley.com/doi/10.1002/hlca.201200602/abstract