RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2008(7): 1065-1068
DOI: 10.1055/s-2008-1032128
DOI: 10.1055/s-2008-1032128
PAPER
© Georg Thieme Verlag Stuttgart · New YorkA Novel Three-Component Reaction Involving Quinoline, Dimethyl Acetylenedicarboxylate, and C-H Acids Leading to the Synthesis of Pyrroloquinoline Derivatives
Weitere Informationen
Received
2 February 2007
Publikationsdatum:
06. März 2008 (online)
Publikationsverlauf
Publikationsdatum:
06. März 2008 (online)

Abstract
The zwitterion derived from quinoline and dimethyl acetylenedicarboxylate on reaction with C-H acids afforded pyrroloquinoline derivatives.
Key words
zwitterion - quinoline - pyrroloquinoline - Michael addition
- 1a
Huisgen R. Angew. Chem., Int. Ed. Engl. 1963, 2: 565 - 1b
Huisgen R. Z. Chem. 1968, 8: 290 - 2a
1,3-Dipolar Cycloaddition Chemistry
Vols. I and II:
Padwa A. Wiley-Interscience; New York: 1984. - 2b
Huisgen R. In Topics in Heterocyclic ChemistryCastle R. John Wiley & Sons; New York: 1969. Chap. 8. p.223 - 3
Huisgen R.Morikawa M.Herbig K.Brunn E. Chem. Ber. 1967, 100: 1094 - 4
Nair V.Sreekanth AR.Abhilash N.Bhadbhade MM.Gonnade RC. Org. Lett. 2002, 4: 3575 - 5
Nair V.Sreekanth AR.Biju AT.Rath NP. Tetrahedron Lett. 2003, 44: 729 - 6
Nair V.Remadevi B.Varma LR. Tetrahedron Lett. 2005, 46: 5333 - 7a
Nair V.Rajesh C.Vinod AU.Bindu S.Sreekanth AR.Mathen JS.Balagopal L. Acc. Chem. Res. 2003, 36: 899 - 7b
Nair V.Menon RS.Sreekanth AR.Abhilash N.Biju AT. Acc. Chem. Res. 2006, 39: 520 - 8
Acheson RM.Elmore NF. Adv. Heterocycl. Chem. 1978, 23: 263 - 9 While this work was under completion, we came across an isolated report in a paper
mentioning the reaction of quinoline and DMAD with ethyl bromopyruvate leading to
the synthesis of a pyrroloquinoline derivative:
Yawari I.Hossaini Z.Sabbaghan M. Tetrahedron Lett. 2006, 47: 6037
References
Single crystal X-ray data for 4 has been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number CCDC 627201.