A versatile synthesis of pyrrolo-, furo- and thienopyridines via photocyclization of 3-amino-2-alkene imines in an acid medium

We describe the synthesis of pyrrolo-, furo- and thieno[3,2- b]pyridines substituted by alkyl-, arylamino or NH 2 groups from irradiation of 2-pyrrolyl-, 2-furyl-, and 2-thienylalkene imines under mild reaction conditions. We also describe the irradiation of 3-pyrrolyl-, 3-furyl-, and 3-thienylalken...

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Bibliographic Details
Published in:Tetrahedron 1999-12, Vol.55 (49), p.14079-14088
Main Authors: Campos, Pedro J., Añón, Elena, Malo, M.Carmen, Rodríguez, Miguel A.
Format: Article
Language:English
Subjects:
Furopyridines
Imines
Pyrrolopyridines
Thienopyridines
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Summary:We describe the synthesis of pyrrolo-, furo- and thieno[3,2- b]pyridines substituted by alkyl-, arylamino or NH 2 groups from irradiation of 2-pyrrolyl-, 2-furyl-, and 2-thienylalkene imines under mild reaction conditions. We also describe the irradiation of 3-pyrrolyl-, 3-furyl-, and 3-thienylalkene imines, which yields pyrrolo[3,2- c]pyridines in all cases. The mechanism for this procedure is proposed. The compounds obtained can potentially be used in medicinal chemistry. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(99)00874-1