Direct Access to 2-Thioxooxazolidin-4-ones and Oxazolidine-2,4-diones from α-Keto Thioesters through Thiolate Transfer

Rajib Maity; Sandip Naskar; Kanchan Mal; Sandipa Biswas; Indrajit Das

doi:10.1002/adsc.201701020

Direct Access to 2-Thioxooxazolidin-4-ones and Oxazolidine-2,4-diones from α-Keto Thioesters through Thiolate Transfer

Rajib Maity, Sandip Naskar, Kanchan Mal, Sandipa Biswas, Indrajit Das

Research output: Contribution to journal › Article › peer-review

16 Scopus citations

Abstract

We report a direct synthesis of 2-thioxooxazolidin-4-ones and oxazolidine-2,4-diones from α-keto thioesters with sodium thiocyanate or potassium cyanate, respectively. The reactions proceed through nucleophilic substitution of a thioester with thiocyanate/cyanate anion, thiolate anion addition to carbonyl carbon, and subsequent intramolecular C−O heterocyclization. (Figure presented.).

Original language	English
Pages (from-to)	4405-4410
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	359
Issue number	24
DOIs	https://doi.org/10.1002/adsc.201701020
State	Published - 19 Dec 2017
Externally published	Yes

Keywords

2-thioxooxazolidin-4-ones
oxazolidine-2,4-diones
rearrangement
synthetic methods
α-keto thioesters

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.201701020

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title = "Direct Access to 2-Thioxooxazolidin-4-ones and Oxazolidine-2,4-diones from α-Keto Thioesters through Thiolate Transfer",

abstract = "We report a direct synthesis of 2-thioxooxazolidin-4-ones and oxazolidine-2,4-diones from α-keto thioesters with sodium thiocyanate or potassium cyanate, respectively. The reactions proceed through nucleophilic substitution of a thioester with thiocyanate/cyanate anion, thiolate anion addition to carbonyl carbon, and subsequent intramolecular C−O heterocyclization. (Figure presented.).",

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T1 - Direct Access to 2-Thioxooxazolidin-4-ones and Oxazolidine-2,4-diones from α-Keto Thioesters through Thiolate Transfer

AU - Maity, Rajib

AU - Naskar, Sandip

AU - Mal, Kanchan

AU - Biswas, Sandipa

AU - Das, Indrajit

PY - 2017/12/19

Y1 - 2017/12/19

N2 - We report a direct synthesis of 2-thioxooxazolidin-4-ones and oxazolidine-2,4-diones from α-keto thioesters with sodium thiocyanate or potassium cyanate, respectively. The reactions proceed through nucleophilic substitution of a thioester with thiocyanate/cyanate anion, thiolate anion addition to carbonyl carbon, and subsequent intramolecular C−O heterocyclization. (Figure presented.).

AB - We report a direct synthesis of 2-thioxooxazolidin-4-ones and oxazolidine-2,4-diones from α-keto thioesters with sodium thiocyanate or potassium cyanate, respectively. The reactions proceed through nucleophilic substitution of a thioester with thiocyanate/cyanate anion, thiolate anion addition to carbonyl carbon, and subsequent intramolecular C−O heterocyclization. (Figure presented.).

KW - 2-thioxooxazolidin-4-ones

KW - oxazolidine-2,4-diones

KW - rearrangement

KW - synthetic methods

KW - α-keto thioesters

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U2 - 10.1002/adsc.201701020

DO - 10.1002/adsc.201701020

M3 - Article

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SN - 1615-4150

VL - 359

SP - 4405

EP - 4410

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 24

ER -

Direct Access to 2-Thioxooxazolidin-4-ones and Oxazolidine-2,4-diones from α-Keto Thioesters through Thiolate Transfer

Abstract

Keywords

ASJC Scopus subject areas

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