Molecular Diversity

, Volume 22, Issue 4, pp 919–927 | Cite as

4-Amino-2,3-dihydro-1λ6-isothiazole-1,1-dioxides and their chemical properties evaluation

  • Maksim S. Dyachenko
  • Alexey V. DobrydnevEmail author
  • Yulian M. Volovenko
Original Article


The reactivity of the 4-amino-2,3-dihydro-1H-1λ6-isothiazole-1,1-dioxide (β-amino-γ-sultam) framework has not been studied sufficiently. Here we describe the chemical properties of this heterocyclic system toward electrophiles on spiranic and non-spiranic substrates. A variety of C-electrophiles (acetic anhydride, benzoyl chloride, DMFDMA, 4,4-dimethoxybutan-2-one) and heteroatom electrophiles (bromine, nitrosyl acetate) have been explored. Both the C-5 and 4-amino positions of the β-amino-γ-sultam system are able to undergo electrophilic reactions. Heteroatom electrophiles attack the C-5 position, whereas carbo-electrophiles affect the amino group. β-Amino-γ-sultams also were used as starting compounds for the synthesis of 6- or 7-substituted 1λ6-isothiazolo[4,5-b]pyridine-1,1-dioxides through condensation reaction and palladium-catalyzed oxidative coupling.

Graphical abstract


Sulfonamides Spiro compounds Enamines Electrophiles Cyclization Coupling 



Alexey Dobrydnev acknowledges Dr. Demid. S. Milokhov for a fellowship and technical support. We would also like to show our gratitude to Mr. Mit Dobrydnev for sharing his pearls of wisdom with us during the course of this research.

Supplementary material

11030_2018_9848_MOESM1_ESM.pdf (7.4 mb)
Supplementary material 1 (PDF 7609 kb)


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Copyright information

© Springer International Publishing AG, part of Springer Nature 2018

Authors and Affiliations

  • Maksim S. Dyachenko
    • 1
    • 2
  • Alexey V. Dobrydnev
    • 1
    • 3
    Email author
  • Yulian M. Volovenko
    • 1
  1. 1.Chemistry DepartmentTaras Shevchenko National University of KyivKievUkraine
  2. 2.Enamine Ltd.KievUkraine
  3. 3.SMC Ecopharm Ltd.KievUkraine

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