Synthesis of Novel 3-Oxobutanohydrazide Derivatives in the Presence of Cerium Ammonium Nitrate

Öz

In this study, a new synthetic method was developed for new 3-oxobutanohydrazide derivatives. This synthetic method consists of two steps. In the first step, aldehyde phenyl hydrazone derivatives were synthesized. Then, these compounds were reacted with 2,2,6-trimethyl-4H-1,3-dioxin-4-one (TMD) compound in the presence of the catalytic amount of cerium ammonium nitrate and 3-oxobutanohydrazide derivatives, which are new target molecules, were synthesized. The structures of the synthesized 3-oxobutanohyidrazide derivatives were characterized by 1H-NMR and 13C-NMR.

Anahtar Kelimeler

• 3-Oxobutanohydrazide
• serium ammonium nitrate
• acetylketene

Seryum Amonyum Nitrat Varlığında Yeni 3-Oksobutanohidrazid Türevlerinin Sentezi

Öz

Bu çalışmada, yeni 3-oksobutanohidrazid türevleri için yeni bir sentetik yöntem geliştirilmiştir. Bu sentetik yöntem iki adımdan oluşmaktadır. İlk aşamada aldehit fenil hidrazon türevleri sentezlendi. Daha sonra, bu bileşikler 2,2,6-trimetil-4H-1,3-dioksin-4-on (TMD) bileşiği ile katalitik miktarda seryum amonyum nitrat varlığında reaksiyona sokularak hedef moleküller olan 3-okzobutanohidrazit türevleri sentezlendi. Sentezlenen 3-oksobutanohidrazid türevlerinin yapıları 1H-NMR ve 13C-NMR ile karakterize edildi.

Anahtar Kelimeler

• 3-Oksobutanohidrazid
• seryum amonyum nitrat
• asetil keten

Kaynakça

1. AAli BH, 1983. Some Pharmacological and Toxicological Properties of Furazolidone. Veterinary Research Communications, 6 (1): 1-11.
2. Annibale AD, Pesce A, Resta S, Trogolo C, 1996. Reaction of 2,2,6-Trimethyl-4H-1,3-dioxin-4-one with imines: an Easy Route to Enamides. Tetrahedron Letters, 41 (79): 7429-7432.
3. Aslanoglu F, 2022. Synthesis of 2-Methyl-pyran-4-ones through Reaction of Acetylketene with Terminal Acetylenes in Presence of Gold (I). ChemistrySelect, 7 (26): 1-4.
4. Aslanoglu F, 2022. Design of 1-(2-pyrrolidinone)-butane-1,3-dione Derivatives and Acetoxylation of These Compound's Methylene via Hypervalent Iodine (III). Journal of Heterocyclic Chemistry, 59 (9): 1660-1663.
5. Chandrika NT, Dennis EK, Brubaker KR, Kwiatkowski S, Watt DS, Tsodikova SG, 2021. Broad-Spectrum Antifungal Agents: Fluorinated Aryl- and Heteroaryl-Substituted Hydrazones. ChemMedChem, 16 (1): 124-133.
6. Çakır B, Dağ Ö, Yıldırım E, Erol K, Şahin MF, 2001. Synthesis and Anticonvulsant Activity of Some Hydrazones of 2-[(3H)-oxobenzoxazolin-3-yl-aceto] Hydrazide. Journal of Faculty of Pharmacy of Gazi University, 18: 99-106.
7. Heiba EI, Dessau RM, 1971, Oxidation by Metal Salts. VIII. Decomposition of Ceric Carboxylates in the Presence of Olefins and Aromatic Hydrocarbons. Journal of the American Chemical Society, 93 (4): 995-999.
8. Ho T. L. 1973. Ceric Ion Oxidation in Organic Chemistry. Synthesis, 6, 347-354.

9. Goswami P, Chowdhury P, 2000, Ceric Ammonium Nitrate (CAN) a Useful Catalyst for The Rapid and High-yield Esterification of Carboxylic Acids and Alcohols with Special Reference to Steroid and Other Multi-functional Natural Products. New Journal of Chemistry, 24: 955-957.
10. Kumar D, Kumar NM, Ghosh S, Shah K, 2012. Novel Bis(indolyl)hydrazide–Hydrazones as Potent Cytotoxic Agents. Bioorganic & Medicinal Chemistry Letters, 22 (1): 212-215.
11. Kumar V, Basavarajaswamy G, Rai MV, Poojary B, Pai VR, Shruthi N, Bhat M, 2015. Rapid ‘one-pot’ Synthesis of a Novel Benzimidazole-5-Carboxylate and Its Hydrazone Derivatives as Potential Anti-inflammatory and Antimicrobial Agents. Bioorganic & Medicinal Chemistry Letters, 25 (7): 1420-1426.
12. McCalla DR, Reuvers A, Kaiser C, 1970. Mode of Action of Nitrofurazone. Journal of Bacteriology, 104 (3): 1126-1134.