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, cilt.17, sa.6, ss.374-380, 2015 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 17 Sayı: 6
  • Basım Tarihi: 2015
  • Doi Numarası: 10.1021/acscombsci.5b00046
  • Dergi Adı: ACS COMBINATORIAL SCIENCE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.374-380
  • Anahtar Kelimeler: 2,3,64-trisubstituted pyridines, 5,6,7,8-tetrahydroquinolines, Mannich bases, pyridine synthesis in water, CHEMISTRY, ARYL
  • Hacettepe Üniversitesi Adresli: Evet

Özet

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.