NITRILES AS MULTIPURPOSE REAGENTS FOR THE SYNTHESIS OF SULTAMS AND SULTONES

Authors

  • Maksym Kovalov Taras Shevchenko National University of Kyiv, 64/13 Volodymyrska St., Kyiv 01601. Enamine Ltd., 78 Winston Churchill St., Kyiv 02094
  • Bohdan V. Vashchenko Taras Shevchenko National University of Kyiv, 64/13 Volodymyrska St., Kyiv 01601. Enamine Ltd., 78 Winston Churchill St., Kyiv 02094

Keywords:

sultams, nitriles, cyano group, cyclization, sulfonamides

Abstract

In this review, we discuss the use of the nitrile function in the synthesis of cyclic sulfonamides (sultams), an important class of antibiotics. The cyano group is a versatile building block in sultam synthesis. It can form the sultam and sulton skeleton or activaten adjacent positions. Commonly, the nitrile group undergoes the carbanion-mediated sulfonate (sulfonamide) intramolecular cyclization reaction, acting as an electrophilic center attacked by a carbanion, forming enamines. Nitriles also facilitate substitutions at α-position through alkylation or cyclization and activate unsaturated bonds in various cycloadditions. Literature indicates that the nitrile group, as a methyleneamine precursor, shows promise for sultam synthesis. This method could efficiently produce spirocyclic sultams with applications in chemistry and biology.

Author Biography

Bohdan V. Vashchenko, Taras Shevchenko National University of Kyiv, 64/13 Volodymyrska St., Kyiv 01601. Enamine Ltd., 78 Winston Churchill St., Kyiv 02094

Currently:
- Assistant (Taras Shevchenko National University of Kyiv, 2022 to date)
- Senior Engineer (Taras Shevchenko National University of Kyiv, 2021 to date)
- Researcher at Scientific Support Department (Enamine Ltd. 2018 to date)

Previous experience:

- PhD (Taras Shevchenko National University of Kyiv, 2019—2023)
- Master's Degree (Taras Shevchenko National University of Kyiv, 2017—2019)
- Synthetic Chemist (Enamine Ltd., 2016—2018)
- Practicing Synthetic Chemist (Taras Shevchenko National University of Kyiv, 2014—2016)
- Bachelor's Degree (Taras Shevchenko National University of Kyiv, 2013—2017)

Scientific interests:
- organic synthesis, lead-oriented synthesis, building blocks for drug discovery, organosulfur (VI), -fluorine and -boron derivatives, alicyclic and heterocyclic compounds, combinatorial and medicinal chemistry, exit vector plots.

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Published

2026-02-24

Issue

Vol. 61 No. 9/10 (2025): Modern catalytic approaches for the assembly and functionalization of heterocyclic compounds

Section

Review Articles