Mannich Bases as Enone Precursors for Water-Mediated Efficient Synthesis of 2,3,6-Trisubstituted Pyridines and 5,6,7,8-Tetrahydroquinolines


HANASHALSHAHABY E. H. A. , ÜNALEROĞLU C.

ACS COMBINATORIAL SCIENCE, vol.17, no.6, pp.374-380, 2015 (Peer-Reviewed Journal) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 17 Issue: 6
  • Publication Date: 2015
  • Doi Number: 10.1021/acscombsci.5b00046
  • Journal Name: ACS COMBINATORIAL SCIENCE
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.374-380
  • Keywords: 2,3,64-trisubstituted pyridines, 5,6,7,8-tetrahydroquinolines, Mannich bases, pyridine synthesis in water, CHEMISTRY, ARYL

Abstract

A highly efficient, regioselective, and environmentally friendly method has been developed for water-mediated synthesis of 2,3,6-trisubstituted pyridines and 5,6,7,8-tetrahydroquinolines. The introduced method allows easy preparation of various polysubstituted pyridines and 5,6,7,8-tetrahydroquinolines via domino reaction of an enolizable ketone, ammonia and enones derived from different Mannich bases in mild reaction conditions. Montmorillonite K-10 promoted this one-pot three-component reaction and gave both new and known 2,3,6-trisubstituted pyridines and 5,6,7,8-tetrahydroquinolines in good yields. The reaction protocol provides a wide array of functionality in construction of polysubstituted pyridines and 5,6,7,8-tetrahydroquinolines from commercially available starting materials in easily applicable and environmentally friendly conditions.