Degradation Reactions

Shioiri, Takayuki

doi:10.1016/b978-0-08-052349-1.00172-4

Cited by 35 publications

(10 citation statements)

References 123 publications

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“…1,11 The procedure, which is outlined in Schemes 1-4, consists of the cyclization of the sulfamoylheterocarboxylic derivatives 2a-c and 7 through a typical Curtius reaction 12,13 followed by alkylation of the intermediate N-2 substituted thiadiazines thus obtained, to give the target N-2,N-4 dialkyl hetero[1,2,4]-thiadiazines.…”

Section: Chemistrymentioning

confidence: 99%

Novel 1,1,3-Trioxo-2H,4H-thieno[3,4-e][1,2,4]thiadiazine Derivatives as Non-Nucleoside Reverse Transcriptase Inhibitors That Inhibit Human Immunodeficiency Virus Type 1 Replication

et al. 1998

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The 1,1,3-trioxo-2H,4H-thieno[3,4-e][1,2,4]thiadiazines (TTDs) represent a recently discovered chemical class of non-nucleoside reverse transcriptase inhibitors that selectively block human immunodeficiency virus type 1 replication. In a search for a better understanding of their mode of binding and with the aim of obtaining novel lead compounds, a second series of TTD derivatives was synthesized and evaluated for antiviral activity. The design of the new compounds was based on a variety of chemical modifications which were carried out in the original prototype 20a (QM 96521). Substitution of a halogen at the meta position of the N-2 benzyl group resulted in an improvement of the antiviral activity by 1 order of magnitude. Compounds bearing at the N-4 position a cyanomethyl, propargyl, or benzyl substituent were found to be the most potent of the series. Modifying the thieno[3,4-e] ring fused to the 1,2,4-thiadiazine moiety to other heterocyclic ring systems decreased the potency. The results obtained in this investigation have provided new indications for the design of even more effective TTDs.

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Section: Chemistrymentioning

confidence: 99%

Novel 1,1,3-Trioxo-2H,4H-thieno[3,4-e][1,2,4]thiadiazine Derivatives as Non-Nucleoside Reverse Transcriptase Inhibitors That Inhibit Human Immunodeficiency Virus Type 1 Replication

et al. 1998

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“…The Curtius rearrangement of an acyl azide into an isocyanate via an acyl nitrene intermediate is a reliable method for the synthesis of amines and their derivatives . It has been widely used in many aspects of chemical industry from synthetic chemistry, medicinal chemistry, to material sectors .…”

Section: Introductionmentioning

confidence: 99%

Thermal Rearrangement of Sulfamoyl Azides: Reactivity and Mechanistic Study

Zou

et al. 2017

J. Org. Chem.

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The rearrangement of sulfamoyl azides under thermal conditions to form a C-C bond while breaking two C-N bonds is reported. Mechanistic study shows that this reaction goes through a Curtius-type rearrangement to form a 1,1-diazene, then which rearranges possibly through both a concerted rearrangement process and a stepwise radical process. This rearrangement could be used in the synthesis of complex biologically active molecules, such as sterols, and piperine derivatives.

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“…Most rearrangement reactions are migrations from an atom to an adjacent one (called 1,2-shifts), but some occur over longer distances. Migrations from a carbon to a nitrogen atom are used to prepare amines from acid derivatives (Scheme c) or ketones (Scheme a,b). , Traditional reactions usually afford one product, whereas two products were generated for this reaction.…”

Section: Introductionmentioning

confidence: 99%

Rearrangement Reaction Based on the Structure of N-Fluoro-N-alkyl Benzenesulfonamide

Yang

2018

J. Org. Chem.

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A novel rearrangement reaction based on the structure of N-fluoro-N-alkyl benzenesulfonamide was developed. The reaction proceeded readily at 50 °C in formic acid and generated a variety of benzenesulfonamides and aldehydes or ketones simultaneously. The reaction mechanism is believed to be a concerted mechanism that consist of 1,2-aryl migration with the departure of fluorine anion via an SN2 mechanism. This rearrangement reaction features an interesting reaction mechanism, mild reaction conditions, simple operations, and a broad substrate scope.

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Degradation Reactions

Cited by 35 publications

References 123 publications

Novel 1,1,3-Trioxo-2H,4H-thieno[3,4-e][1,2,4]thiadiazine Derivatives as Non-Nucleoside Reverse Transcriptase Inhibitors That Inhibit Human Immunodeficiency Virus Type 1 Replication

Novel 1,1,3-Trioxo-2H,4H-thieno[3,4-e][1,2,4]thiadiazine Derivatives as Non-Nucleoside Reverse Transcriptase Inhibitors That Inhibit Human Immunodeficiency Virus Type 1 Replication

Thermal Rearrangement of Sulfamoyl Azides: Reactivity and Mechanistic Study

Rearrangement Reaction Based on the Structure of N-Fluoro-N-alkyl Benzenesulfonamide

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