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Title: Stereocontrolled oxidative additions upon N-alkyl-1,4-dihydropyridines: Synthesis of hexahydrofuro[2,3-b]pyridine derivatives
Authors: Kumar, Rakesh
Kumar, Dhiraj
Prasad, Ashok K
Keywords: 1,4-Dihydropyridines;Tetrahydorpyridines;Enamine;Radical cyclisations
Issue Date: Aug-2012
Publisher: NISCAIR-CSIR, India
Abstract: trans-2-Alkoxy-3-halotetrahydropyridines are synthesized in a very efficient single step by stereo- and regiocontrolled N-halosuccinimide (NXS) promoted allyl alcohol addition to the enamine group in N-alkyl-1,4-dihydropyridines. These compounds have been cyclised using sodium cyanoborohydride in the presence of azobisisobutyronitrile (AIBN) (cat.) and tributylstannane (cat.) affording hexahydrofuro[2,3-b]pyridine derivatives. The bicyclic adducts that formed are useful precursors for further transformations to form biologically active heterocyclic such as alkaloids and azasugars.
Page(s): 1123-1130
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.51B(08) [August 2012]

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