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

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.

Key words

multicomponent reactions - heterocycles - tetrazole - Ugi reaction - proline derivatives

References

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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: [phone]; E-mail: [e-mail]].