Reaction pathway of POCl3-mediated Knoevenagel condensation of bisulfite adducts with 2,4-thiazolidinedione

被引：2

作者：

Mohanty, Sandeep ^{[1
]}

Roy, Amrendra Kumar ^{[1
]}

Reddy, Sandeep ^{[1
]}

Kumar, Kuchipudi Pavithran Vinay ^{[1
]}

Karmakar, Arun Chandra ^{[2
]}

机构：

[1] Dr Reddys Labs Ltd, Proc Res & Dev, API Plant, Bollaram 3,Plot 116,126C,Survey 157, Hyderabad 502325, Andhra Pradesh, India

[2] Shasun Pharmaceut Ltd, Pondicherry, India

来源：

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2016年 / 191卷 / 06期

关键词：

Knoevenagel condensation; statistical design of experiment; H-1; NMR; ReactIR; LC-MS; DERIVATIVES; EFFICIENT; PROTOCOL;

D O I：

10.1080/10426507.2015.1073277

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

We investigated the POCl3-mediated transformation of aromatic bisulfite adducts to the corresponding 5-arylidenethiazolidine-2,4-diones. The in situ transformation of an aromatic bisulfite adduct to the parent aldehyde in a non-aqueous non-polar solvent (toluene) was demonstrated using DoE (Design of experiment), offline H-1 NMR, online ReactIR, HPLC, LC-MS, and GC-MS. By means of these analytical tools, we determined, for the first time, the structure of the intermediate species (aldehyde) prior to the carbon-carbon double-bond formation. The carbon-sulfur bond undergoes a fast cleavage, immediately after the addition of POCl3, which finally affords the corresponding 5-arylidenethiazolidine-2,4-diones.

引用

页码：857 / 866

页数：10

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