Synthesis of carbo- and heterofused 5-amino-2H-1,2-thiazine 1,1-dioxides via the CSIC reaction strategy

Dyachenko, Maksim S.; Chuchvera, Yaroslav O.; Dobrydnev, Alexey V.; Frolov, Andriy I.; Ostapchuk, Eugeniy N.; Popova, Maria V.; Volovenko, Yulian M.

doi:10.1016/j.tet.2022.132685

Cited by 7 publications

(3 citation statements)

References 68 publications

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“…Other hydrolysis methods e.i . aqueous HCl, [5] ethanolic HCl, [5a,7f] or aqueous HOAc [9] provided similar result.…”

Section: Resultsmentioning

confidence: 72%

“…The difference in the spectral properties of enamino sultones 1,2 and 3,4 was also reflected in their chemical behavior. Whereas amino group in sultones 1 and 2 predominantly related to amide‐type nitrogen, sultones 3,4 retained the general properties of enamines and showed the activity similar to those of α‐unsubstituted β‐enamino γ‐sultones, [5d] β‐enamino γ‐sultams, [9] and β‐enamino δ‐sultams [7f] . Thus, TFA‐mediated hydrolysis of enamine fragment [10] was succeeded only for α‐aryl‐substituted enamino sultones and afforded the corresponding β‐enolo γ‐sultone 15 a in 85 % yield.…”

Section: Resultsmentioning

confidence: 95%

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A Study on Sulfonylation of Cyanohydrins with α‐Functionalized Sulfonyl Chlorides

et al. 2022

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Herein we describe the reaction of cyanohydrins with α‐functionalized sulfonyl chlorides and discuss the reactivity of target α‐functionalized β‐enamino γ‐sultones. Depending on electron‐withdrawing activity of α‐functionality of given sulfonyl chlorides the reaction with cyanohydrins either accomplished in one‐pot manner (tandem sulfonylation–CSIC reaction) affording β‐enamino γ‐sultones (α‐functionality=CO2Me, CN, p‐C6H4‐CO2Me) or resulted in sulfonylated cyanohydrins, which can be converted into target β‐enamino γ‐sultones through the t‐BuOK‐mediated CSIC reaction (α‐functionality=Ph). The nature of α‐functionality drastically affects the reactivity of α‐functionalized β‐enamino γ‐sultones. Specifically, α‐CO2Me and α‐CN β‐enamino γ‐sultones are less reactive toward electrophiles and tolerate the nucleophiles. This is the consequence of high degree of conjugation between amino group and EWG within the sultone framework. At the same time, α‐aryl β‐enamino γ‐sultones possess significantly lower degree of conjugation (due to steric hindrance between aryl core and sultone framework) and therefore retain reactivity of the enamine fragment.

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“…Other hydrolysis methods e.i . aqueous HCl, [5] ethanolic HCl, [5a,7f] or aqueous HOAc [9] provided similar result.…”

Section: Resultsmentioning

confidence: 72%

Section: Resultsmentioning

confidence: 95%

A Study on Sulfonylation of Cyanohydrins with α‐Functionalized Sulfonyl Chlorides

et al. 2022

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“…Otherwise (if the nitrogen atom is blocked by an alkyl substituent) only the annulation of the fivemembered ring to the bornane skeleton is observed. [132] Finally, as a logical continuation of our research program on the synthesis of sultams [133][134][135][136][137][138][139] and sultones [140,141] through the CSIC (Carbanion-mediated Sulfonate (or Sulfonamide) Intermolecular Coupling and Intramolecular Cyclization) [142][143][144][145][146] reaction strategy we turned our attention to functionalized sulfinamides as the potential substrates. Bringing these ideas to life our remarkable PhD student Y. Chuchvera performed the LiHMDS-mediated cyclization of sulfinylated Strecker amines 214 into the corresponding β-enamino-γ-sultims 215, albeit in poor yield (Scheme 85).…”

Section: Miscellaneous Methodsmentioning

confidence: 99%

Cyclic Sulfinamides

Dobrydnev,

Popova,

Volovenko

2023

The Chemical Record

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The literature on cyclic sulfinamides (put simply, sultims) published from 1989 to 2022 has been summarized and reviewed. The information is divided into two sections: the analysis of synthetic methods on the preparation of cyclic sulfinamides and the discussion of the chemical properties of cyclic sulfinamides focusing on their reactions and applications. The survey of the reaction conditions, provided in the most detailed way, and a critical view of the reaction mechanisms add an extra dimension to the text. The data presented will be useful to specialists in different areas, especially those who work in the field of synthetic organic and pharmaceutical chemistry.

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Selective Access to Sultams and Spirocyclic Sultams by the Divergent Annulations of (N‐Aryl)‐Alkynyl Sulphonamides

Raji Reddy,

Rathaur,

Karuna Sagar

et al. 2024

Adv Synth Catal

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Herein, we present the first annulation reaction of (N‐aryl)‐alkynyl sulphonamides leading to sultams or spirocyclic sultams. The selective formation of aforesaid products is based on the variable reactivity, intramolecular ortho‐cyclization or dearomative ipso‐annulation, guided by the substituent on N‐aryl group of the substrate. The ortho‐annulation is mediated by electrophile, while the ipso‐annulation is promoted by the radical, enabling the functionalization (selenyl or iodo) on sultams. The synthetic potential of this method is illustrated by modifications of the functional groups present in the products obtained

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Synthesis of carbo- and heterofused 5-amino-2H-1,2-thiazine 1,1-dioxides via the CSIC reaction strategy

Cited by 7 publications

References 68 publications

A Study on Sulfonylation of Cyanohydrins with α‐Functionalized Sulfonyl Chlorides

A Study on Sulfonylation of Cyanohydrins with α‐Functionalized Sulfonyl Chlorides

Cyclic Sulfinamides

Selective Access to Sultams and Spirocyclic Sultams by the Divergent Annulations of (N‐Aryl)‐Alkynyl Sulphonamides

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