Synthesis of biologically active fused 1,4-oxathiin derivatives from 4-hydroxydithiocoumarins, arylacetylenes and dimethyl sulfoxide by Cu(<scp>i</scp>)-catalyzed C–H functionalization and cross-dehydrogenative C–S coupling reactions

Mondal, Santa; Yashmin, Sabina; Ali, Rashid; Soundaram, R; Ghosh, Siddhartha Sankar; Khan, Abu T.

doi:10.1039/d1ob00846c

Cited by 12 publications

(1 citation statement)

References 29 publications

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“…Taking cues from the reliable methods for the synthesis of 1,4‐oxathiin [19c] and 2,3‐dihydrobenzothiazine, [28] we have chosen the reaction conditions for the ring‐closing reaction of β‐hydroxysulfides and β‐aminosulfides as shown in Scheme 3.…”

Section: Resultsmentioning

confidence: 99%

Regioselective Ring‐Opening of Epoxide and N‐Tosylaziridine with 4‐Hydroxydithiocoumarin: Key Precursors for 2,3‐Dihydro‐1,4‐oxathiin and 2,3‐Dihydro‐1,4‐thiazine Derivatives

et al. 2022

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Regioselective ring‐opening reaction between 4‐hydroxydithiocoumarins with various epoxides and N‐tosylaziridines is achieved for the synthesis of β‐hydroxysulfides and β‐N‐tosylaminosulfides. The present protocols showed high regioselectivity, broad substrates scope compatibility, and mild reaction conditions. In addition, some of the ring‐opening products are utilized for the conversion of 2,3‐dihydro‐1,4‐oxathiin and 2,3‐dihydro‐1,4‐thiazine derivatives in presence of 10 mol% CuI in DMF at 120°C. Moreover, the antiproliferative activity study of the newly synthesized compounds, namely β‐hydroxysulfides (3 d, 3 i & 3 m) and β‐aminosulfides (5 a & 5 e), have been investigated. Furthermore, flow cytometry analysis‐based measurements of elevated reactive oxygen species (ROS) upon treatment of MCF‐7 and HeLa cells with 3 d, 3 i, and 3 m are commensurate with their anti‐cancer properties.

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Section: Resultsmentioning

confidence: 99%

Regioselective Ring‐Opening of Epoxide and N‐Tosylaziridine with 4‐Hydroxydithiocoumarin: Key Precursors for 2,3‐Dihydro‐1,4‐oxathiin and 2,3‐Dihydro‐1,4‐thiazine Derivatives

et al. 2022

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Recent Advances of C−S Coupling Reaction of (Hetero)Arenes by C−H Functionalization

Zhang,

Wang,

Lucan

et al. 2024

The Chemical Record

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Organic sulfur compounds encompass a vast and diverse variety of species that possess unique biological activity due to the presence of sulfur atoms or sulfur‐containing functional groups. These compounds are widely present in natural products, pharmaceuticals, agricultural chemicals, and functional materials. In recent years, numerous sulfur‐containing compounds such as thiols, thioethers, disulfides, thiourea, dimethyl sulfoxide, sulfonates and their derivatives, as well as sulfur‐containing inorganic compounds, have been utilized as coupling agents to synthesize (hetero)aryl sulfides via C−H Functionalization. These novel transformations provide effective methods for constructing C−S bond of (hetero)arenes, while also expanding the scope of (hetero)aryl sulfides with the potential biological activity. Therefore, the synthesis of aryl sulfides through C−H bond functionalization has attracted widespread attention. This review mainly focuses on the construction of (hetero)aryl sulfides via C−H bond functionalization since 2015. We hope this review offers a useful conceptual overview and inspires further advancements in the efficient construction of C−S bonds.

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Six-membered ring systems: with O and/or S atoms

Santos¹,

Silva²

2023

Progress in Heterocyclic Chemistry

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Synthesis of biologically active fused 1,4-oxathiin derivatives from 4-hydroxydithiocoumarins, arylacetylenes and dimethyl sulfoxide by Cu(i)-catalyzed C–H functionalization and cross-dehydrogenative C–S coupling reactions

Abstract: The hitherto unreported 2-aryl-10H-thiochromeno[3,2-b][1,4]oxathiin-10-one derivatives are accomplished in a single pot from 4-hydroxydithiocoumarins, arylacetylenes and dimethyl sulfoxide in the presence of 10 mol% CuI and K2CO3 in an oil-bath at...

Cited by 12 publications

References 29 publications

Regioselective Ring‐Opening of Epoxide and N‐Tosylaziridine with 4‐Hydroxydithiocoumarin: Key Precursors for 2,3‐Dihydro‐1,4‐oxathiin and 2,3‐Dihydro‐1,4‐thiazine Derivatives

Regioselective Ring‐Opening of Epoxide and N‐Tosylaziridine with 4‐Hydroxydithiocoumarin: Key Precursors for 2,3‐Dihydro‐1,4‐oxathiin and 2,3‐Dihydro‐1,4‐thiazine Derivatives

Recent Advances of C−S Coupling Reaction of (Hetero)Arenes by C−H Functionalization

Six-membered ring systems: with O and/or S atoms

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