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Indian Journal of Chemistry -Section B (IJC-B) >
IJC-B Vol.51B [2012] >
IJC-B Vol.51B(08) [August 2012] >
| 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 |
| CC License: |  CC Attribution-Noncommercial-No Derivative Works 2.5 India |
| ISSN: | 0975-0983(Online); 0376-4699(Print) |
| Source: | IJC-B Vol.51B(08) [August 2012]
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