Simple and efficient cleavage reaction of the boc group in heterocyclic compounds

Dedicated to the memory of Pr. Ladjama Daif A series of chiral cyclosulfamides have been synthesized by alkaline cyclisation starting from N‐benzoylamino acids (Ala, Val, Leu, Phe) derivatives and chlorosulfonyl isocyanate. A simplified and regioselective deprotection of the cyclic compounds (cyclosulfamides) containing the tert‐butyloxycarbonyl group (Boc) has been achieved in good yield by fusion under reduced pressure.     

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 publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.     

Synthesis and Biological Activity of New Chiral N‐Acylsulfonamide Bis‐oxazolidin‐2‐ones

A new series of chiral 5‐substituted bis‐oxazolidinones containing an acylsulfonamide moiety has been synthesized starting from chlorosulfonyl isocyanate, (l )‐ethyl lactate, and oxazolidin‐2‐ones. All the reactions were conducted at ambient temperature, and the N‐acylsulfonamide bis‐oxazolidin‐2‐ones were obtained with high yields within 2 h. Some of the newly synthesized compounds were evaluated in vitro against the virulent strain RH of Toxoplasma gondii and the human lymphocytes, and showed promising results.     

Synthesis and antitumor evaluation of novel sulfonylcycloureas derived from nitrogen mustard

A new series of sulfonylcycloureas derivatives have been synthesized and evaluated in vitro for their antitumor activity against four cancer cell lines (A431, Jurkat, U266, and K562). These compounds were prepared by the condensation of several sulfonamides (2a–m) with ethyl bis(2-chloroethyl)carbamate (1a). The relative cytotoxicity of these new derivatives in comparison to chlorambucil is reported.     

Efficient Synthesis of Modified Sulfamides and Cyclosulfamides Containing Phosphonate Moieties

Abstract

The synthesis of two new series of functionalized phosphonates is described. A new entry for the synthesis of 5-phosphonoalkyl cyclosulfamides and bis(phosphonoalkyl) sulfamides starting from dihalogeno bis(amino) sulfone has been developed. These compounds have been synthesized in good yields. Triethylphosphite has been used to introduce the phosphonate moiety into sulfamides and cyclosulfamides via Arbuzov reaction.     

Simple and efficient synthesis of new chiral N,N′‐sulfonyl bis‐oxazolidin‐2‐ones

A series of new chiral N,N′‐sulfonyl bis‐oxazolidin‐2‐ones were synthesized starting from 2‐aminoalcohols, sulfuryl chloride, and diethyl carbonate. This method utilizes natural amino acids as a source of chirality for the preparation of oxazolidinones. © 2006 Wiley Periodicals, Inc. Heteroatom Chem 17:61–65, 2006; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20183     

Cyclosulfamides as Constraint Dipeptides: The Synthesis and Structure of Chiral Substituted 1,2,5-Thiadiazolidine 1,1-Dioxides: Evaluation of the Toxicity

A general synthesis for the preparation of chiral N-N′ substituted 1,2,5-thiadiazolidine 1,1-dioxides has been developed beginning with proteogenic amino acid, sulfuryl chloride, and dibromoethane. The selected chemistry and spectral properties of these compounds are examined. Overall, routes described are applicable to the synthesis of a variety of constrained dipeptidal sulfamides representing novel peptidomimetic scaffolds.     

Synthèse Et Cyclisation De Carboxylsulfamides Dérivés D'amines Et D'α-Hydroxyesters. Éavaluation De L'Activité Bactéeriostatique

Abstract

Les carboxylsulfamides sont obtenus à partir de l'isocyanate de chlorosulfonyle, d'amines primaires et d'α-hydroxyesters. Après réduction alcaline, ces carboxylsulfamides sont cyclisés dans les conditions de la réaction de Mitsunobu pour conduire aux N-sulfamoyloxazolidinones chides avec des rendements élevés.

The synthesis of carboxylsulfamides was carried out starting from chlorosulfonyl isocyanate, primary amines and α-hydroxyesters. After reduction, the carboxylsulfamides were cyclised under Mitsunobu conditions giving N-sulfamoyloxazolidinones in good yields.     

Microwave-accelerated multicomponent synthesis and X-ray characterization of novel benzothiadiazinone dioxide derivatives,analogues of Monastrol

Research on Chemical Intermediates - We demonstrate here a rapid and comfortable synthetic sequence to benzothiadiazinone dioxide (six-membered cyclic sulfamide) derivatives, analogues of...     

Synthese et N-Acylation Regiospecifique de 1,2,5-Thiadiazolidines 1,1-Dioxydes Chirales

The regiospecific synthesis of chiral N-acyl cyclosulfamides (sulfa-analogues of cyclic ureas) was carried out starting from chlorosulfonyl isocyanate (CSI), 1-substituted N-benzyl-2-chloroethylamine hydrochloride and acyl chloride. Chiral N-acyl-thiadiazolidines 1,1-dioxides have been prepared in high yield starting from the corresponding cyclosulfamides acyl chloride, triethylamine and a catalytic amount of 4-(N,N-dimethylamino)pyridine. L'accès régiospécifique aux cyclosulfamides chiraux N-acylés (analogues sulfonés d'urèes cycliques) a été développé à partir de l'isocyanate de chlorosulfonyle, de N-benzyl-2-chloroéthylamine chirale substituée en position 1 et de chlorure d'acide. Les N-acyl thiadiazolidines 1,1-dioxydes chirales ont été préparées avec des rendements élevés à partir du cyclosulfamide correspondant par traitement avec un chlorure d'acide en présence de triéthylamine et une quantité catalytique de 4-(N,N-dimethylamino)pyridine.