Javad SAFAEI-GHOMI, Fariba SALIMI, Ali RAMAZANI

100102

The reaction of dialkyl acetylenedicarboxylates with 2-oxo-2-phenylacetaldehyde in the presence of primary amines: synthesis of alkyl 2-benzoyl-4-alkylamino-5-oxo-2,5-dihydro-3-furan carboxylate derivatives

A 3-component domino reaction approach between a primary amine, a dialkyl acetylenedicarboxylate, and 2-oxo-2- phenylacetaldehyde that affords novel alkyl 2-benzoyl-4-alkylamino- 5-oxo-2,5-dihydro-3-furan carboxylate derivatives is reported. The reaction sequence consists of an initial Michael addition of primary amines to dialkyl acetylenedicarboxylates, followed by an aldol-like reaction with 2-oxo-2-phenylacetaldehyde, and then g -lactonization to afford the products. This cascade reaction sequence represents a rapid and unprecedented route to the described biologically interesting molecules.
Anahtar Kelimeler:

Dialkyl acetylenedicarboxylates, 2-oxo-2-phenylacetaldehyde, primary amines, furan, Michael addition

The reaction of dialkyl acetylenedicarboxylates with 2-oxo-2-phenylacetaldehyde in the presence of primary amines: synthesis of alkyl 2-benzoyl-4-alkylamino-5-oxo-2,5-dihydro-3-furan carboxylate derivatives

A 3-component domino reaction approach between a primary amine, a dialkyl acetylenedicarboxylate, and 2-oxo-2- phenylacetaldehyde that affords novel alkyl 2-benzoyl-4-alkylamino- 5-oxo-2,5-dihydro-3-furan carboxylate derivatives is reported. The reaction sequence consists of an initial Michael addition of primary amines to dialkyl acetylenedicarboxylates, followed by an aldol-like reaction with 2-oxo-2-phenylacetaldehyde, and then g -lactonization to afford the products. This cascade reaction sequence represents a rapid and unprecedented route to the described biologically interesting molecules.
Keywords:

Dialkyl acetylenedicarboxylates, 2-oxo-2-phenylacetaldehyde, primary amines, furan, Michael addition,

PDF
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: 6
  • Yayıncı: TÜBİTAK
Arşiv
Sayıdaki Diğer Makaleler

The reaction of dialkyl acetylenedicarboxylates with 2-oxo-2-phenylacetaldehyde in the presence of primary amines: synthesis of alkyl 2-benzoyl-4-alkylamino-5-oxo-2,5-dihydro-3-furan carboxylate derivatives

Javad SAFAEI-GHOMI, Fariba SALIMI, Ali RAMAZANI

Silica nanoparticles as a high efficient catalyst for the one-pot synthesis of 3-oxo-3-phenylpropanamid derivatives from isocyanides, phenylacetaldehyde and secondary amines

Ali RAMAZANI, Kourosh DASTANRA, Fatemeh Zeinali NASRABADI

Synthesis, characterization, and antioxidant activities of new trisubstituted triazoles

Kemal SANCAK, Yasemin ÜNVER, Dilek ÜNLÜER, Esra DÜĞDÜ, Gülcan KÖR

Design and synthesis of new 1,2,4-triazole derivatives containing morpholine moiety as antimicrobial agents

Deniz ŞAHİN, Hacer BAYRAK, Ahmet DEMİRBAŞ, Neslihan DEMİRBAŞ

Optimization of a new cloud point extraction procedure for the selective determination of trace amounts of total iron in some environmental samples

Celal DURAN, Duygu ÖZDEŞ, Elif Çelenk KAYA, Halit KANTEKİN

Synthesis, anti-inflammatory, antiplatelet and in silico evaluations of (E)-3-(3-(2,3-dihydro-3-methyl-2-oxo- 3H-benzoxazole-6-yl)-1-phenyl-1H-pyrazole- 4-yl)acrylamides

Sultan BAYTAŞ, Nilüfer Nermin Turan DURAL, Yeşim ÖZKAN

Reaction kinetics of carbon dioxide with 2-amino-2-hydroxymethyl-1,3-propanediol in aqueous solution obtained from the stopped flow method

Cyril Sunday UME, Erdoğan ALPER

Competitive hydrogen bonding in aspirin-aspirin and aspirin-leucine interactions

Zeynep YURTSEVER, Burak ERMAN, Ersin YURTSEVER

Transmission FT-IR spectroscopic analysis of human kidney stones in the Hyderabad region of Pakistan

Muhammad Hassan KHASKHELI, Syed Tufail Hussain SHERAZI, Huma Mazhar UJAN

Copolymerization of N-Vinyl pyrrolidone with methyl methacrylate by Ti(III)-DMG redox initiator

Ajithkumar Manayan PARAMBIL, Yashoda Malagar PUTTAIAHGOWDA