Synthesis 2006(19): 3215-3223  
DOI: 10.1055/s-2006-950219
PAPER
© Georg Thieme Verlag Stuttgart · New York

8,9,10,10a-Tetrahydro-6H-tetrazolo[1,5-a]pyrrolo[2,1-c]pyrazines: New Heterocyclic Frameworks Generated by an Ugi-Type Multicomponent Reaction

Vilius Franckevičius, Deborah A. Longbottom, Richard M. Turner, Steven V. Ley*
University of Cambridge, Department of Chemistry, Lensfield Road, Cambridge, CB2 1EW, UK
Fax: +44(1223)336442; e-Mail: svl1000@cam.ac.uk;
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Publikationsverlauf

Received 10 July 2006
Publikationsdatum:
04. September 2006 (online)

Abstract

A one-pot, Ugi-type three-component coupling process between an aldehyde, an isocyanide and proline tetrazole is reported, leading to new heterocyclic structures in good to excellent yields.

10

In addition to the two usual isomers, reaction in methanol (Table [2] , entry 1) also afforded a racemic tetrazole decomposition product 30 (Figure [6] ), identity of which was confirmed by full characterisation, including an X-ray crystal structure (see reference 11).

Figure 6 Decomposition product 30

11

Crystallographic data (excluding structure factors) for the structures 20, 25 and 30 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-612544, CCDC-612545 and CCDC-612546, respectively. Copies of the data can be obtained free of charge on application to the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK. [Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk].