Enantioselectivity of 3‐amino‐2‐oxazolidinone derivatives with potential psychotropic activity on cellulose tris(4‐methylbenzoate) chiral selector

Chilmończyk, Zdzisław; Ksycińska, Hanna; Krzywda, Jerzy

doi:10.1002/1520-636x(2001)13:3<148::aid-chir1012>3.3.co;2-p

Cited by 3 publications

(5 citation statements)

References 9 publications

(12 reference statements)

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“…The title compound was prepared according to the method of Chilmonczyk et al (1997). The molecular structure of the title compound (III).…”

Section: Methodsmentioning

confidence: 99%

“…In the Pharmaceutical Research Institute in Warsaw, a series of derivatives of 3-amino-2-oxazolidinone have been prepared (Chilmonczyk et al, 1997). It has been found that the oxazolidinone derivative 5-morpholinomethyl-3-(4-chlorobenzylideneamino)-2-oxazolidinone, (II) hereafter, is a potential psychotropic drug (Chilmonczyk, 1995).…”

Section: Commentmentioning

confidence: 99%

“…Data collection: KM-4 Software (Kuma, 1993); cell re®nement: KM-4 Software; data reduction: DATAPROC (Kuma, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990a); program(s) used to re®ne structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1990b) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97. In the Pharmaceutical Research Institute in Warsaw, a series of derivatives of 3-amino-2-oxazolidinone have been prepared (Chilmonczyk et al, 1997). It has been found that the oxazolidinone derivative 5-morpholinomethyl-3-(4chlorobenzylidenamino)-2-oxazolidinone, (I) hereafter, is a potential psychotropic drug (Chilmonczyk, 1995).…”

Section: Data Collectionmentioning

confidence: 99%

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4-[3-(4-Fluorobenzylideneamino)-2-oxo-1,3-oxazolidin-5-ylmethyl]morpholin-4-ium chloride monohydrate

et al. 2001

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“…The title compound was prepared according to the method of Chilmonczyk et al (1997). The molecular structure of the title compound (III).…”

Section: Methodsmentioning

confidence: 99%

Section: Commentmentioning

confidence: 99%

Section: Data Collectionmentioning

confidence: 99%

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4-[3-(4-Fluorobenzylideneamino)-2-oxo-1,3-oxazolidin-5-ylmethyl]morpholin-4-ium chloride monohydrate

et al. 2001

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“…In the Pharmaceutical Research Institute in Warsaw, a series of derivatives of 3-amino-2-oxazolidinone have been prepared (Chilmonczyk et al, 1997). It has recently been found that the oxazolidinone derivative 5-morpholinomethyl-3-(4-chloridebenzylideneamino)-2-oxazolidinone is a potential psychotropic drug (Chilmonczyk, 1995).…”

Section: Commentmentioning

confidence: 99%

4-[3-(4-Chlorobenzylideneamino)-2-oxooxazolidin-5-ylmethyl]morpholin-4-ium chloride monohydrate

et al. 2001

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“…These compounds display a variety of biological activity [1][2][3][4] and are used in asymmetric synthesis [5]. Formation of the 2-oxazolidinone ring is used when necessary to protect both the adjacent amino and hydroxy groups [6][7][8].…”

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Synthesis of isomeric 2-oxazolidinones from (1R,2R)-and (1S,2S)-2-amino-1-(4-nitrophenyl)-1,3-propanediols

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Zaitsev

Zaitseva

et al. 2007

Chem Heterocycl Comp

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Keywords: (1R,2R)-and (1S,2S)-2-amino-1-(4-nitrophenyl)-1,3-propanediols, (4R,5R)-and (4S,5S)-4-hydroxymethyl-5-(4-nitrophenyl)oxazolidin-2-ones, (1'R,4R)-and (1'S,4S)-4-[hydroxy(4-nitrophenyl)-methyl]oxazolidin-2-ones.2-Oxazolidinones have attracted considerable attention in chemistry. These compounds display a variety of biological activity [1][2][3][4] and are used in asymmetric synthesis [5]. Formation of the 2-oxazolidinone ring is used when necessary to protect both the adjacent amino and hydroxy groups [6][7][8].In our previous work [9], we synthesized (1S,2S)-2-ethoxycarbonylamino-1-(4-nitrophenyl)-1,3-propanediol (2) from (1S,2S)-2-amino-1-(4-nitrophenyl)-1,3-propanediole (1) with subsequent conversion to isomeric 2-oxazolidinones: (1'S,4S)-4-[hydroxy(4-nitrophenyl)methyl)oxazolidin-2-one (4) and (4S,5S)-4-hydroxymethyl-5-(4-nitrophenyl)oxazolidin-2-one (3) according to Scheme 1.It is known that the closure of the oxazolidinone ring upon treatment of a suitable methylcarbamate proceeds rather rapidly even at room temperature and in a slightly basic medium (pH 9.5) in only 20 min [8]. But we maintained the reaction mixture under similar conditions for about 120 h, and only a slight amount of oxazolidinone 4 was obtained as a precipitate [9].In this conection the aim of the present work was the search of the conditions most favorable for formation of the one of the isomeric 2-oxazolidinones, permitting a reduction of the reaction time.Base is a catalyst in the formation of 2-oxazolidinones but it may lead to undesired racemization. Propanediol 2 is sensitive to the pH value and the solution at pH > 10 turns reddish; the product isolated is less pure. Thus, propanediol 2 is initially [9] treated with a 1:1 mixture of water and saturated methanolic potassium carbonate, which has pH ~9.5.In a search for optimal reaction conditions, the pH of the reaction solution was raised to 10 by addition solid potassium hydroxide. Furthermore, different amounts of propanediol 2 were treated with equal volumes of the indicated solution. In experiment 5, 20 ml water was added to 50 ml used solution to reduce the solubility of oxazolidinone 4 (Table 1).

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Enantioselectivity of 3‐amino‐2‐oxazolidinone derivatives with potential psychotropic activity on cellulose tris(4‐methylbenzoate) chiral selector

Cited by 3 publications

References 9 publications

4-[3-(4-Fluorobenzylideneamino)-2-oxo-1,3-oxazolidin-5-ylmethyl]morpholin-4-ium chloride monohydrate

4-[3-(4-Fluorobenzylideneamino)-2-oxo-1,3-oxazolidin-5-ylmethyl]morpholin-4-ium chloride monohydrate

4-[3-(4-Chlorobenzylideneamino)-2-oxooxazolidin-5-ylmethyl]morpholin-4-ium chloride monohydrate

Synthesis of isomeric 2-oxazolidinones from (1R,2R)-and (1S,2S)-2-amino-1-(4-nitrophenyl)-1,3-propanediols

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