Tek Kapta Yeni Bir Yöntemle Alkollerden Potansiyel Biyolojik Aktif Azidosülfonil Bileşiklerinin Sentezi

Bu çalışmada, çeşitli alkoller ile klorosülfonil izosiyanat (CSI) ve sodyum azid varlığında tek kapta yeni bir yöntemle azidosülfonil bileşiklerinin sentezi gerçekleştirilmiştir. Reaksiyon verimin artırılması için kullanılan asit, baz ve çözücü parametreleri incelenmiş ve optimize reaksiyon şartlarında yüksek verimlerle azidosülfonil bileşiklerinin sentezi gerçekleştirilmiştir. Sentezleri gerçekleştirilen bileşiklerin yapı karakterizasyonları 1H NMR, 13C NMR, IR ve Elementel analiz sonuçları ile yapılmıştır.

Anahtar Kelimeler:

Azidosulfonil, alkol, klorosulfonil izosiyanat, sodyum azit

The Novel Method and One-pot Synthesis of Potential Biological Active Azidosulfonyl Compounds from Alcohols

In this study, the one-pot synthesis of azidosulphonyl compounds by a new method was carried out in the presence of chlorosulfonyl isocyanate (CSI) and sodium azide with various alcohols. The acid, base and solvent parameters used to increase the reaction yield were investigated and synthesis of azidosulfonyl compounds was carried out in high yields under optimized reaction conditions. The structure characterization of the synthesized molecules was performed with 1H NMR, 13C NMR, IR and Elemental analysis.

Keywords:

Sulfamoylazide, alcohol, chlorosulfonyl isocyanate, sodium azide,

PDF

___

Akbaba Y, Bastem E, Topal F, Gulcin I, Maras A, Goksu S, 2014. Synthesis and Carbonic Anhydrase Inhibitory Effects of Novel Sulfamides Derived from 1-Aminoindanes and Anilines. Archiv Der Pharmazie, 347: 950-57.
Bauer JM, Frey W, Peters R, 2016. Dual Palladium(II)/Tertiary Amine Catalysis for Asymmetric Regioselective Rearrangements of Allylic Carbamates. Chemistry-a European Journal, 22: 5767-77.
Culhane JC, Fokin VV, 2011. Synthesis and Reactivity of Sulfamoyl Azides and 1-Sulfamoyl-1,2,3-triazoles. Organic Letters, 13: 4578-80.
Daryadel S, Atmaca U, Taslimi P, Gulcin I, Celik M, 2018. Novel sulfamate derivatives of menthol: Synthesis, characterization, and cholinesterases and carbonic anhydrase enzymes inhibition properties. Archiv Der Pharmazie, 351.
Goddard-Borger ED, Stick RV, 2007. An efficient, inexpensive, and shelf-stable diazotransfer reagent: Imidazole-1-sulfonyl azide hydrochloride. Organic Letters, 9: 3797-800.
Golob T, Liebl R, von Angerer E, 2002. Sulfamoyloxy-substituted 2-phenylindoles: Antiestrogen-based inhibitors of the steroid sulfatase in human breast cancer cells. Bioorganic & Medicinal Chemistry, 10: 3941-53.
Hartwig JF 1998. Carbon-heteroatom bond-forming reductive eliminations of amines, ethers, and sulfides. Accounts of Chemical Research, 31: 852-60.
Kienle M, Dubbaka SR, Brade K, Knochel P, 2007. Modern amination reactions. European Journal of Organic Chemistry: 4166-76.
Matier WL, Comer WT, Deitchman D, 1972. Sulfamoyl Azides-Hydrolysis Rates and Hypotensive Activity. Journal of Medicinal Chemistry, 15: 538.
Wolf OT, Kirschbaum C, 1999. Actions of del dehydroepiandrosterone and its sulfate in the central nervous system: effects on cognition and emotion in animals and humans. Brain Research Reviews, 30: 264-88.
Zhao J, Li ZY, Song SL, Wang MA, Fu B, Zhang ZH, 2016. Product-Derived Bimetallic Palladium Complex Catalyzes Direct Carbonylation of Sulfonylazides. Angewandte Chemie-International Edition, 55: 5545-49.