122320-73-4Relevant articles and documents
Synthetic optimization of rosiglitazone and related intermediates for industrial purposes
Meng, Ge,Zheng, Meilin,Dong, Mengshu,Gao, Yang,Zheng, Aqun,Li, Zhenyu,Hu, Ruizhi
, p. 2023 - 2033 (2016)
As an important newly Food and Drug Administration (FDA)-approved drug for treating diabetes, rosiglitazone (1) has received much attention from researchers in many areas. To search for an economical and convenient synthesis method for 1, we explored the reaction conditions and workup of a scalable five-step synthetic route by an orthogonal method to determine the best condition for each reaction step. The starting materials are commercially available, including 2-chloropyridine (2), N-methylethanolamine (3), 4-fluorobenzaldehyde (4a) or 4-hydroxybenzaldehyde (4b), and 1,3-thiazolidine-2,4-dione (5). The five sequential reaction steps are cyclization, alkylation, etherification, condensation, and reduction, having optimal yield of 90, 99, 59, 75, and 91 %, respectively. The best overall yield to synthesize rosiglitazone based on compound 2 was 40 %, being suitable for industrial purposes, using water as a green solvent and avoiding column chromatography during the last three reaction steps.
Microwave-assisted synthesis of the antihyperglycemic drug rosiglitazone
Gaonkar, Santosh L.,Shimizu, Hiroki
, p. 3314 - 3317 (2010)
We developed a simple, rapid, high yielding, and environmentally benign microwave assisted total synthesis of rosiglitazone, an antihyperglycemic agent for diabetes mellitus Type II. We used microwave heating successfully to improve reactions in four of six steps and obtain quicker and higher yields. In addition, all intermediates were isolated in good yields with crystallizations only and did not require chromatographic separations.
Preparation method of rosiglitazone
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, (2020/12/29)
The invention provides a preparation method of rosiglitazone. The preparation method is characterized by comprising the following steps: reacting 2-chloropyridine with 2-methylaminoethanol under the catalysis of sodium triphenylmethyl to generate 2-[N-methyl-N-(2-pyridine) amino] ethanol; then carrying out Williamson synthesis reaction on the 2-[N-methyl-N-(2-pyridine) amino] ethanol and 4-fluorobenzaldehyde under the catalysis of bis (trimethylsilyl) amino potassium to obtain 4-[2-[N-methyl-N-(2-pyridine) amino] ethoxy] benzaldehyde; then carrying out condensation reaction with thiazoline-2,4-diketone to obtain 5-{4-[2-[N-methyl-N-(2-pyridine) amino] ethoxy] benzylidene} thiazoline-2, 4-diketone; and carrying out reduction reaction under the catalysis of an organic manganese reagent to obtain the rosiglitazone. The preparation method is simple, mild in condition, high in reaction yield and suitable for industrial production.
Organocatalytic Cyclization of COS and Propargylic Derivatives to Value-Added Heterocyclic Compounds
Zhou, Hui,Zhang, Rui,Mu, Sen,Zhang, Hui,Lu, Xiao-Bing
, p. 5728 - 5732 (2019/06/04)
The organocatalytic cyclization of propargylic amines/amides with carbonyl sulfide (COS) was firstly achieved by employing COS adducts of Lewis base (LB) as organocatalysts, affording various functionalized 1,3-thiazolidine-2-ones, and 1,3-thiazolidine-2,4-diones derivatives in a highly chemo- and stereoselective manner. The isotope labeling and stoichiometric experiments suggested the LB-COS adducts preferentially mediated basic ionic pair mechanism. Furthermore, the practical application of this methodology was highlighted by the highly efficient synthesis of rosiglitazone using COS as sulfur source.
Robust Acenaphthoimidazolylidene Palladacycles: Highly Efficient Catalysts for the Amination of N-Heteroaryl Chlorides
Deng, Qinyue,Zhang, Yang,Zhu, Haibo,Tu, Tao
supporting information, p. 2364 - 2368 (2017/09/06)
A series of robust N-heterocyclic carbene palladacycles have been successfully developed. These showed high catalytic activity and selectivity toward the challenging amination of N-heteroaryl chlorides. Different primary and secondary amines were fully compatible with this catalytic system. Remarkably, no double amination products could be detected when primary amines were utilized in our catalytic transformation. Furthermore, the protocol has been successfully extended to synthesize rosiglitazone, a clinical drug for diabetes mellitus, highlighting its potential pharmaceutical feasibility.
An alternative synthetic route for an antidiabetic drug, rosiglitazone
Jawale, Dhanaji V.,Pratap, Umesh R.,Mane, Ramrao A.
experimental part, p. 924 - 928 (2012/03/26)
A convenient and scalable four-step novel route has been developed for the synthesis of rosiglitazone (8), an antidiabetic drug. This multistep route requires 4-fluoro benzaldehyde (4), 2,4-thiazolidinedione (6) and 2-chloro pyridine (1) as key reactants and gives overall better yield of rosiglitazone. In addition, some steps have been accelerated, which leads to an overall time saving of 10 h.
A METHOD FOR PREPARATION OF THIAZOLIDINEDIONE DERIVATIVES
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Page/Page column 6-7, (2009/10/18)
The present invention offers the conjugate reduction of α-β-unsaturated thiazolidinedione derivatives which involves the reagents cobalt ion in the form of cobaltous chloride hexahydrate, the ligand dimethyl glyoxime in N, N dimethyl formamide, the reducing agent sodium borohydride and the solvent media for the reaction is polyethylene glycol (PEG).
Process for the Preparation of Intermediates of Rosiglitazone, Rosiglitazone and New Polymorphic Forms Thereof
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Page/Page column 5, (2009/09/28)
The invention relates to a polymorphic form of 5-(4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzylidene)-2,4-thiazolidinedione (Formula (I)): to a process for its preparation and to the use of such compound for preparing rosiglitazone in the form of a free base or a salt thereof. The invention also relates to a polymorphic form of rosiglitazone in the form of a free base, to a process for its preparation and to the use of such polymorph for preparing a salt of rosiglitazone. The invention also relates to a process of preparing a polymorphic form of a rosiglitazone salt.
An improved process for hydrogenation of 5-(substituted Benzylidene) 2,4- Thiazolidine Dione compounds to give corresponding ( +/- ) 5- (substituted Benzyl ) 2,4-Thiazolidine Dione
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Page/Page column 6, (2008/06/13)
The present provides a preparation of (+/-) -5- [substituted. phenyl methyl ] - 2,4-thiazolidinediones from 5-[ substituted benzylidene ]-2,4-thiazolidinediones by catalytic hydrogenation using precious metal catalyst, using DMF or formic acid [ or aqueous formic acid] and perchloric acid.
A PROCESS FOR THE PREPARATION OF SUBSTITUTED PHENYL ETHER COMPOUNDS AND ROSIGLITAZONE
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Page/Page column 14, (2008/06/13)
A novel process for the preparation of a compound of the formula (II), which is useful as intermediate compound for the preparation of thiazolidinedione derivatives, such as rosiglitazone, pioglitazone, troglitazone and ciglitazone, is disclosed. The novel process comprising reacting a compound of the formula (III) with a compound of the formula (IV) in a mixture of a non-polar water immiscible organic solvent and water (two phase system) with an alkali metal hydroxide or an alkali metal carbonate as a base in the presence of a phase transfer catalyst. In the first aspect of the present invention comprising reacting 2-(N-methyl-N-(2- pyridyl) ethanol with 4-fluorobenzaldehyde in the mixture of a non-polar water immiscible organic solvent, preferably toluene, and water with an alkali metal hydroxide or an alkali metal carbonate as a base, preferably potassium hydroxide, in the presence of a phase transfer catalyst, e.g. tetra n-butylammonium hydrogensulphate or benzyltriethylammonium chloride, to obtain 4-[2-(N-methyl-N-(2- pyridyl)amino)ethoxy]benzaldehyde, which is the key intermediate for preparing rosiglitazone and its salts, e.g. maleate salt or phosphate salt, useful in the treatment of Type II diabetes.
