New approaches to polysubstituted pyrroles and pyrrolinones from alpha-cyanomethyl-beta-ketoesters

Demir A. S., Emrullahoglu M., Ardahan G.

TETRAHEDRON, cilt.63, sa.2, ss.461-468, 2007 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 63 Sayı: 2
  • Basım Tarihi: 2007
  • Doi Numarası: 10.1016/j.tet.2006.10.054
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.461-468
  • Anahtar Kelimeler: pyrroles, heteroannulation, GABA analogs, 1,3-dicarbonyls, pyrrolinones, AMINO-ALCOHOLS, EFFICIENT SYNTHESIS, HOMOCHIRAL AMINES, DERIVATIVES, COMPLEXES, (R)-1-ACETYL-5-ISOPROPOXY-3-PYRROLIN-2-ONE, 2-AMINOPYRROLE-4-CARBOXYLATES, PYRROLIDIN-2-ONES, NUCLEOPHILES, REACTIVITY
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

In this present paper, we report the efficient, regioselective one-pot synthesis of 5-alkoxy and 5-alkylsulfanylpyrrole-3-carboxylates in high yields via the zinc perchlorate-catalyzed addition of alcohols and thiols to the nitrile carbon of alpha-cyanornethyl-beta-ketoesters followed by annulation. The addition-annulation process is undertaken in aqueous solution to give 4,5-dihydro-5-oxo-1H-pyrrole-beta-carboxylates (pyrrolinones) in good yields. These 4,5-dihydro-5-oxo-1H-pyrrole-3-carboxylates are also obtained by the hydrolysis of 5-alkoxypyrrole-3-carboxylates. (c) 2006 Elsevier Ltd. All rights reserved.