Download PDF
Synfacts 2010(11): 1234-1234  
DOI: 10.1055/s-0030-1258834
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Pyrrolo[1,2-a]pyrazines from Vinyl Azides

Contributor(s): Victor Snieckus, Matthew O. Kitching
W. Chen, M. Hu, J. Wu, H. Zou*, Y. Yu*
Zhejiang University, Hangzhou, P. R. of China
Further Information

Publication History

Publication Date:
21 October 2010 (online)

    Permissions and Reprints

Significance

The synthesis of pyrrolo[1,2-a]pyrazines from the reaction of 2-pyrrolecarbaldehyde with vinyl azides under basic conditions is described. Base and solvent screens revealed the use of cesium carbonate and DMF to be optimal. Investigation of the substrate scope demonstrated that the reaction requires the use of vinyl azides bearing α-EWGs (e.g., R = H, no reaction). A mechanism is proposed based on the results of the substrate scope; however, no additional evidence is offered in justification.