Nour-Eddine Aouf

Synthesis of 1,2,5-Thiadiazolidines 1,1-dioxides (Cyclosulfamides) Starting from Amino Acids and Chlorosulfonyl Isocyanate

Abstract We report here a practical access to a series of five-membered cyclosulfamides (1,2,5-thiadiazolidines 1,1-dioxides) N2 substituted by the BOC group. These compounds are synthesized starting from chlorosulfonyl isocyanate and nitrogen mustards or amino acids. The derivatization of amino acids can lead to an alkyl group on C-4 with a well-defined configuration; in this case the N5 position was protected by a benzyl group. These compounds are valuable tools for asymmetric synthesis.

General synthesis of n-membered cyclic sulfamides

A general method for the synthesis of n-membered cyclic sulfamides (cyclosulfamides) is described. An application to the synthesis of constrained peptidal cyclic sulfamide is illustrated.

A simple and eco-sustainable method for the sulfonylation of amines under microwave-assisted solvent-free conditions

A new environmentally benign, simple, and efficient protocol for the chemoselective sulfonylation of various structural amines using microwave irradiation under solvent- and catalyst-free conditions is reported. The corresponding sulfonamides were obtained in excellent yields within short reaction times. Simplicity, milder, cleaner and greener conditions, easier work-up, and lower generation of waste or pollution are the main advantages of this method.

A one-pot three-component synthesis of novel α-sulfamidophosphonates under ultrasound irradiation and catalyst-free conditions

An efficient and convenient one-pot synthesis of novel α-sulfamidophosphonates is described via a three-component reaction. This reaction was carried out through a three component condensation reaction of sulfonamide, an aromatic aldehyde and triethylphosphite under conventional/ultrasonic techniques, catalyst-free and solvent-free conditions. This methodology was established with many advantages, including mild reaction conditions, short reaction times, good yields, simple work-up procedures, and environmental friendliness.

A simple, rapid, and efficient N-Boc protection of amines under ultrasound irradiation and catalyst-free conditions

Abstract A green and simple approach for the N-Boc protection on structurally diverse amines under ultrasound irradiation is described. Selective N-Boc protection was achieved in excellent isolated yield in a short reaction time at room temperature. Mild conditions, inexpensive and an easily available reagent, and absence of any auxiliary substances are the main advantages of this procedure.Graphical abstract

N,N’-Substituted 1,2,5 Thiadiazolidine 1,1-Dioxides: Synthesis, Selected Chemical and Spectral Proprieties and Antimicrobial Evaluation †

The sulfamide functional group is increasingly relevant in both medicinal and bioorganic chemistry. We report here practical access to a series of N2,N5-substituted five-membered cyclosulfamides. The five-membered heterocyclic motif was prepared starting from proteogenic amino acids and chlorosulfonyl isocyanate via the Mitsunobu reaction. Selected chemical and spectral proprieties and the antimicrobial evaluation of these compounds are detailed.

N‐Chlorosulfonyloxazolidin‐2‐ones: Synthesis, Structure, and Reactivity Toward Aminoesters

Abstract Synthesis, structure, and reactivity of chiral N‐chlorosulfonyloxazolidin‐2‐ones are described. Their synthesis were easily carried out starting from the corresponding chiral oxazolidin‐2‐ones and sulfuryl chloride to afford the title compounds 1 in high yields.

A simple and eco-sustainable method for the O-Boc protection/deprotection of various phenolic structures under water-mediated/catalyst-free conditions

A greener, efficient, and chemoselective protocol for O-Boc protection/deprotection of a wide range of phenol derivatives is reported under catalyst-free conditions in water-related systems. Unlike previous reports, no additional reagents or catalysts were used, and workup fulfils green chemistry requirements, making the present method even more interesting.

Efficient Method for The Synthesis of α-Amidophosphonates via the Michaelis-Arbuzov Reaction

Abstract A new series of modified α-amidophosphonates (or β-ketophosphonate) was synthesized by an efficient method, starting from aminoesters and chloroacetyl chloride. We have established that chloroacetyl chloride is a suitable reagent allowing the introduction a halogen moiety for the Arbuzov reaction. The α-amidophosphonates were prepared in two steps (acetylation, phosphorylation). Supplemental materials are available for this article. Go to the publishers online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. GRAPHICAL ABSTRACT

One-pot synthesis of novel oxazaphosphinanes under ultrasound irradiation and solvent-free conditions

A rapid and efficient solvent-free one-pot synthesis of novel oxazaphosphinane is described under ultrasound irradiation. This reaction was carried out through a three-component condensation reaction of amino alcohol, aromatic aldehyde, and triethyl phosphite. Ultrasonic effects were established with many advantages, including high yields, shorter reaction times, easy and quick isolation of the products. The newly synthesized compounds were systematically characterized by IR, 1H NMR, 13C NMR, 31P NMR, MS, and elemental analysis.Graphical abstract