A novel one-pot synthesis of highly diverse indole scaffolds by the Ugi/Heck reaction

Tetrahedron Letters

Volumn 47, Issue 27, 2006, Pages 4683-4686

  Kalinski, Cédric ^a,b   Umkehrer, Michael ^a   Schmidt, Jürgen ^a   Ross, Günther ^a   Kolb, Jürgen ^a   Burdack, Christoph ^a   Hiller, Wolfgang ^b   Hoffmann, Stephan D ^b  

^a Priaton GmbH   (Germany)

^b TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Combinatorial chemistry; Indole; Isocyanide based multi component reactions (IMCRs); Ugi Heck reaction; Ugi reaction

Indexed keywords

ALDEHYDE; ANILINE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CINNAMALDEHYDE; CYANIDE; FORMIC ACID; INDOLE;

ARTICLE; CHEMICAL REACTION KINETICS; HECK REACTION; MOLECULAR INTERACTION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 33744519893     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.04.127     Document Type: Article

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12. 3 were added. The reaction mixture was stirred for additional 16-24 h at 80 °C. Afterwards, the solvent was evaporated again, the resulting residue was dissolved in ethyl acetate and filtered through a pad of silica. The resulting crude product was purified by crystallisation from ethanol or by column chromatography on silica gel (hexane/ethyl acetate).
13. +. Mp: 194.6 °C.
14. +.
15. w = 0.141 for all observed reflections. Crystallographic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication No. CCDC 600942. Further details on the crystal structure investigation may be obtained from the Cambridge Crystallographic Data Centre free of charge, on application to CCDC, 12 Union Road, Cambridge CB12EZ, UK (fax: (+44) 1223 336 033; e-mail: deposit@ccdc.cam.ac.uk), quoting the depository number.
16. +. Mp: 196.1 °C.
17. +.
18. Keating T.A., and Armstrong R.W. J. Am. Chem. Soc. 118 (1996) 2574
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20. 5), 106.93, 113.31 (Cq), 114.26, 115.08, 118.81, 120.51, 122.22 (Cq), 122.41 (Cq), 123.05, 123.29, 130.30 (Cq), 136.72 (Cq), 158.59 (C{double bond, long}O). MS (ESI): m/z = 250 [M-H].