Regioselective synthesis of novel spiroindane-1,3-diones through 1,3-dipolar cycloaddition reactions

Tetrahedron Letters

Volumn 51, Issue 36, 2010, Pages 4734-4737

  Sarrafi, Yaghoub ^a   Hamzehlouian, Mahshid ^a   Alimohammadi, Kamal ^a   Khavasi, Hamid Reza ^b  

^a UNIVERSITY OF MAZANDARAN   (Iran)

^b SHAHID BEHESHTI UNIVERSITY   (Iran)

Author keywords

1,3 Dipolar cycloaddition; Azomethine ylide; Ninhydrin; Spiroindane 1,3 dione

Indexed keywords

1,3 INDANDIONE DERIVATIVE; 2' BENZOYL 1' PHENYL 2',5',6',10'B TETRAHYDRO 1'H SPIRO[INDENE 2,3' PYRROLE[2,1 A] ISOQUINOLINE] 1,3 DIONE; AZOMETHINE YLIDE; CHALCONE DERIVATIVE; NINHYDRIN; SPIROINDANE 1,3 DIONE; TETRAHYDROISOQUINOLINE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CRYSTAL STRUCTURE; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; HETERONUCLEAR MULTIPLE BOND CORRELATION; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 77955473845     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.07.018     Document Type: Article

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43. Typical experimental procedure for 4a: A mixture of ninhydrin (1) (1 mmol, 0.178 g), 1,2,3,4-tetrahydroisoquinoline (2) (1 mmol, 0.139 g), and chalcone 3a (1 mmol, 0.208 g) was heated at reflux with stirring in EtOH (10 ml) for 4 h. The resulting orange precipitate was then filtered and recrystallized from EtOH to afford the pure product in good yield (yield 90%, mp: 162 °C).
44. +).
45. Crystallographic data for the structure 4h in this Letter have been deposited with the Cambridge Crystallographic Data centre as supplementary Publication No. CCDC-777612. Copies of the data can be obtained, free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 01223 336033 or email: deposit@ccdc.cam.ac.uk ).