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

✍ Scribed by Pedro J. Campos; Elena Añón; M.Carmen Malo; Miguel A. Rodríguez

Book ID
104209717
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
422 KB
Volume
55
Category
Article
ISSN
0040-4020

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✦ Synopsis

We describe the synthesis of pyrrolo-, furo-and thieno[3,2-b]pyridines substituted by alkyl-, arylamino or NH2 groups from irradiation of 2-pyrrolyl-, 2furyl-, 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.

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A Simple Synthesis of Aminoazapolycyclic Compounds via a Photochemically Induced Cyclization Reaction of 3-Amino-2-alkene Imines in an Acid Medium. -Irradiation of alkene-imines such as (I), (III), (V), and (VII) in the presence of HBF 4 permits the synthesis of aminoazapolycyclic compounds under mi