Reactions of perfluoronitroxides with sulphur dioxide

Arfaei, A.; Smith, S.

doi:10.1039/p19840001791

Cited by 13 publications

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“…The high performance of sulfamate esters in amination reactions and their propensity to form six-membered oxathiazinane products inspired our investigation of sulfamates fashioned from N -alkylhydroxylamines . Catalytic C−H insertion of such substrates affords unique [1,2,3,6]-oxathiadiazinane-2,2-dioxide heterocycles that can, in principle, be reduced to yield differentially protected 1,2-diamines . Rhodium-catalyzed intramolecular C−H insertion of ureas and guanidines also gives cyclic products, which may be ring-opened to furnish analogous diamine derivatives; however, hydrolysis of such heterocycles generally requires forcing conditions incompatible with other attendant functional groups. ,, …”

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confidence: 99%

Catalytic C−H Amination for the Preparation of Substituted 1,2-Diamines

2008

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Vicinal diamines appear frequently as structural units in biological and medicinal molecules of interest and as auxiliary groups or ligands for catalytic processes. 1 The rich and varied applications for 1,2-diamines belie the rather modest number of general methods for the efficient preparation of such compounds. 2 Accordingly, we have attempted to capitalize on the power of sulfamate ester C-H amination to address this problem (Figure 1).

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Catalytic C−H Amination for the Preparation of Substituted 1,2-Diamines

2008

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“…Meanwhile, Smith et al reported the reaction of SO 2 and SF 4 with dioxyl 80 and obtained two heterocycles 82a and 82b ( Scheme 21 ) [ 119 ]. In neither case was a copolymer formed, something which differed from the results from the reaction of dioxyl 80 with tetrafluoroethene and hexafluoropropene in a previous report [ 113 ].…”

Section: Seven- and Larger-membered Heterocyclesmentioning

confidence: 99%

A Brief Review on the Synthesis of the N-CF3 Motif in Heterocycles

et al. 2023

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The trifluoromethyl group is widely recognized for its significant role in the fields of medicinal chemistry and material science due to its unique electronic and steric properties that can alter various physiochemical properties of the parent molecule, such as lipophilicity, acidity, and hydrogen bonding capabilities. Compared to the well-established C-trifluoromethylation, N-trifluoromethylation has received lesser attention. Considering the extensive contribution of nitrogen to drug molecules, it is predicted that constructing N-trifluoromethyl (N-CF3) motifs will be of great significance in pharmaceutical and agrochemical industries. This review is mainly concerned with the synthesis of heterocycles containing this motif. In three-membered heterocycles containing the N-CF3 motif, the existing literature mostly demonstrated the synthetic strategy, as it does for four- and larger-membered heterocycles. Certain structures, such as oxaziridines, could serve as an oxidant or building blocks in organic synthesis. In five-membered heterocycles, it has been reported that N-CF3 azoles showed a higher lipophilicity and a latent increased metabolic stability and Caco-2-permeability compared with their N-CH3 counterparts, illustrating the potential of the N-CF3 motif. Various N-CF3 analogues of drugs or bioactive molecules, such as sildenafil analogue, have been obtained. In general, the N-CF3 motif is developing and has great potential in bioactive molecules or materials. Give the recent development in this motif, it is foreseeable that its synthesis methods and applications will become more and more extensive. In this paper, we present an overview of the synthesis of N-CF3 heterocycles, categorized on the basis of the number of rings (three-, four-, five-, six- and larger-membered heterocycles), and focus on the five-membered heterocycles containing the N-CF3 group.

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“…The lack of convenient methods for the preparation of 1,2-diamine derivatives, however, remains a problem in synthesis, complicated by an unavoidable reliance on serial functional group interconversion. The application of C–H amination technology for 1,2-diamine assembly can, in principle, streamline access to such structures. , Our efforts to delineate a general solution for preparing differentially substituted 1,2-diamines have led to the identification of a novel family of N-protected hydroxylamine sulfamates that react under the action of a dirhodium catalyst to give [1,2,3,6]-oxathiadiazinane-2,2-dioxide heterocycles . Herein, we describe the synthesis and unique properties of N -Troc-derived oxathiadiazinanes as masked 1,2-diamine equivalents.…”

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Synthesis of Differentially Substituted 1,2-Diamines through Advances in C–H Amination Technology

2012

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A general, high yielding method for the synthesis of 1,2-diamine derivatives is described that capitalizes on selective, rhodium-catalyzed C-H insertion of hydroxylamine-based sulfamate esters. The resulting Troc-protected oxathiadiazinane heterocycles are easily modified and can be reduced under the mild action of NaI to afford differentially substituted diamine products. This technology offers a number of salient improvements over related C-H and π-bond amination tactics for diamine synthesis.

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Reactions of perfluoronitroxides with sulphur dioxide

Cited by 13 publications

References 0 publications

Catalytic C−H Amination for the Preparation of Substituted 1,2-Diamines

Catalytic C−H Amination for the Preparation of Substituted 1,2-Diamines

A Brief Review on the Synthesis of the N-CF3 Motif in Heterocycles

Synthesis of Differentially Substituted 1,2-Diamines through Advances in C–H Amination Technology

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