General synthesis of n-membered cyclic sulfamides

Régaı̈nia, Zine; Winum, Jean‐Yves; Smaine, Fatma-Zohra; Toupet, Loı̈c; Aouf, Nour‐Eddine; Montéro, Jean-Louis

doi:10.1016/s0040-4020(03)00982-7

Cited by 26 publications

(12 citation statements)

References 19 publications

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“…Six-membered ring heterocycles are formed selectively and product yields range from 80 to 85% [85]. These novel compounds may have utility as medicinally active agents and/or as precursors to complex 1,3-diamines and derivatives thereof [86][87][88][89].…”

Section: Sulfamides and Sulfonamidesmentioning

confidence: 99%

Rhodium(II)‐Catalyzed Oxidative Amination

Espino

Bois

2005

Modern Rhodium‐Catalyzed Organic Reactions

105

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17 Rhodium(II)-Catalyzed Oxidative Amination 380 Scheme 17.1 Copper-catalyzed decomposition of arylsulfonyl azides. Scheme 17.2 Intramolecular C-H amination of an iminoiodinane. 17.3 Intermolecular C-H Amination with Rhodium(II) Catalysts 381 Scheme 17.3 Metal porphyrin-catalyzed allylic amination. Scheme 17.4 C-H amination by a radical-rebound mechanism. 17 Rhodium(II)-Catalyzed Oxidative Amination 382 Scheme 17.5 Rhodium-catalyzed N-atom transfer using NsN=IPh. Scheme 17.6 Stereospecific C-H amination under rhodium-catalyzed conditions. 17.3 Intermolecular C-H Amination with Rhodium(II) Catalysts 383 Scheme 17.7 Radical clock study of metallo-nitrene C-H insertion. Scheme 17.8 Intermolecular C-H insertion by chiral rhodium catalysts. 17.5 Intramolecular C-H Amination with Rhodium(II) Catalysts 385 Scheme 17.11 Allylic and benzylic amination using PhI(OAc) 2 . 17.5 Intramolecular C-H Amination with Rhodium(II) Catalysts 387 Tab. 17.1 C-H amination of 18 carbamate esters. Entry Substrate Product Entry Substrate Product 17.5 Intramolecular C-H Amination with Rhodium(II) Catalysts 389 Scheme 17.14 Ketone formation by 28 alcohol-derived carbamates. 17.7 Enantioselective C-H Insertion with Sulfamate Esters 401 Scheme 17.29 Oxidative cyclization of unsaturated sulfonamides. Scheme 17.30 Preliminary investigations of asymmetric C-H amination. 17.11 Applications of C-H Amination in Synthesis 407 17.11 Applications of C-H Amination in Synthesis 409 Scheme 17.39 Asymmetric synthesis of (-)-tetrodotoxin. 17 Rhodium(II)-Catalyzed Oxidative Amination 410 Scheme 17.40 Nucleophilic ring opening of N-acylated oxathiazinanes. Scheme 17.41 Nickel-catalyzed cross-coupling of phenol-derived sulfamate esters.

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Section: Sulfamides and Sulfonamidesmentioning

confidence: 99%

Rhodium(II)‐Catalyzed Oxidative Amination

Espino

Bois

2005

Modern Rhodium‐Catalyzed Organic Reactions

105

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“…Our studies have focused on the preparation of substituted cyclic sulfamides [12][13][14][15]. As a continuation of this research interest, here we report our results regarding the synthesis of N-arylthiadiazolidine 1,1-dioxides via C(sp2)-N(sp2) bond formation using…”

mentioning

confidence: 93%

“…Starting N 2 -substituted, N 5 H -1,2,5-thiadiazolidines were prepared from the chlorosulfonyl isocyanate (CSI) according to established synthetic procedures [12][13][14][15][18][19][20].…”

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confidence: 99%

Copper-(s)-N-methylpyrrolidine-2-carboxylate catalyzed N-Arylation of N<sup>5</sup>h-1,2,5-thiadiazolidine 1,1-dioxides

Dehamchia¹,

Régaı̈nia²

2016

J. Fundam and Appl Sci.

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A copper-catalyzed N-arylation of N 5 H-1,2,5-thiadiazolidine 1,1-dioxides derivatives (cyclic sulfamides) is described. Reactions were carried out using Ullmann-Goldberg-type condensation with (S)-N-methyl-2-carboxylate as the ligand, and N-arylated products were obtained with moderate to good yields. The structures of the synthesized compounds were confirmed based on analytical and spectral data.

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“…Furthermore, the pyrrolo[1,2- b ][1,2,5]benzothiadiazepine (PBTD) derivatives were also reported to exert potent anticancer activities [12]. Considering the diverse biological properties of this class of compounds and as part of continuous work on the synthesis of biologically active heterocycles [13], we herein report simple and efficient procedures for the synthesis of a new class of fused benzothiadiazepine derivatives (a), (b), (c) (Figure 1). These derivatives include two thiadiazepine rings and macrocyclic molecules containing a sulfamide functionality (–N–SO 2 –N–), which were synthesised using previously described N , N ' -disubstituted symmetric sulfamides and N (Boc), N ′(alkyl)sulfamide [14–18].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New Fused Benzothiadiazepines and Macrocyclic Sulfamides Starting from N,N-Disubstituted Sulfamides and N(Boc)-Sulfamides

Dehamchia

Régaı̈nia

2012

ISRN Organic Chemistry

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Herein, we describe an efficient one-step synthesis of new fused benzothiadiazepine-1,1-dioxides and macrocyclic sulfamides. The synthesis of these compounds was achieved in moderate yields starting from previously described N,N′-disubstituted symmetric sulfamides and N-tert-butoxycarbonyl, N′-alkyl sulfamide. The chemical structures of all the new compounds reported in this work were confirmed by NMR, IR, and mass spectrometry. These compounds are beneficial building blocks that can be used in deriving new chemical entities that exert a wide spectrum of pharmacological activities.

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General synthesis of n-membered cyclic sulfamides

Cited by 26 publications

References 19 publications

Rhodium(II)‐Catalyzed Oxidative Amination

Rhodium(II)‐Catalyzed Oxidative Amination

Copper-(s)-N-methylpyrrolidine-2-carboxylate catalyzed N-Arylation of N<sup>5</sup>h-1,2,5-thiadiazolidine 1,1-dioxides

Synthesis of New Fused Benzothiadiazepines and Macrocyclic Sulfamides Starting from N,N-Disubstituted Sulfamides and N(Boc)-Sulfamides

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