Unexpected simultaneous synthesis of trisubstituted quinolines and acylhydrazones under catalyst-free conditions


Largani T. H., IMANZADEH G., Pesyan N. N., ŞAHİN E.

SYNTHETIC COMMUNICATIONS, cilt.47, sa.11, ss.1077-1084, 2017 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 47 Sayı: 11
  • Basım Tarihi: 2017
  • Doi Numarası: 10.1080/00397911.2017.1310249
  • Dergi Adı: SYNTHETIC COMMUNICATIONS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1077-1084
  • Atatürk Üniversitesi Adresli: Evet

Özet

Trisubstituted quinolines and acylhydrazones were unexpectedly prepared from a reaction of N '-((2-aminophenyl)(phenyl)methylene) benzohydrazides with acetylenic esters. Using of N '-((2-aminophenyl)(phenyl)methylene) benzohydrazides led to obtain not only quinoline, but also a second pharmaceutical important product acylhydrazone. Notably, excellent yields, operational simplicity, short reaction times, and the avoidance of the use of catalysts make this approach an attractive complementary method to produce quinoline-2,3-dicarboxylates. The crystal structure of 5a was determined using single-crystal X-ray crystallography. The results showed that crystal packing diagram of 5a is of two pairs of molecules that have two independent alternate intermolecular 1D-polymeric H-bonds between two perpendicular molecules.