Solvent-free organic salt media mono symmetrical aza-Michael: synthesis of new N-mono substituted phthalhydrazide derivatives

SOLTANZADEH Z., IMANZADEH G., NOROOZİ-PESYAN N., ŞAHİN E.

GREEN CHEMISTRY LETTERS AND REVIEWS, cilt.10, sa.2, ss.107-116, 2017 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 10 Sayı: 2
  • Basım Tarihi: 2017
  • Doi Numarası: 10.1080/17518253.2017.1307459
  • Dergi Adı: GREEN CHEMISTRY LETTERS AND REVIEWS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.107-116
  • Atatürk Üniversitesi Adresli: Evet

Özet

In this paper, C-N bond formation between 2,3-dihydrophthalazine-1(4H),4-dione (phthalhydrazide) and alpha,beta-unsaturated esters was investigated and a new series of phthalazine derivatives was synthesized using an efficient and simple method under solvent-free conditions. An aza-Michael addition of phthalhydrazide to both acrylic and fumaric esters led to N-monosubstituted phthalhydrazides (as mono-Michael adduct) in the presence of tetrabutylammonium bromide as a high polar media, and 1,4-diaza-bicyclo[2,2,2] octane as an available organic base. In this reaction, the N1,N2-bis-Michael adduct was not observed at all. Also, reactions were performed at 90 degrees C and yields of products were good to excellent.