- C-S and C-N coupling reactions of barbituric acid via selective and complete bromination using greener KBr/H2O2 as a brominating agent
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1,3-Disubstituted/unsubstituted barbituric acids on treatment with KBr-H2O2 as a greener brominating reagent give mono and dibromo barbituric acids. With aqueous HCl selective bromination and without aqueous HCl complete bromination of active methylene group of barbituric acids took place. The reaction of monobarbituric acids with thiosemicarbazide and thioglyoxalic acid under refluxing in aqueous medium, simple C-S coupling products were obtained.The spiro C-N coupling product was obtained by the interaction of dibromo barbituric acid with thiosemicarbazide and C-N condensation product was obtained by the interaction of dibromo barbituric acid with guanidine nitrate, both reactions took place in aqueous medium under refluxing conditions. An environmentally benign, aqueous mediated C-S and C-N organic transformation by the interaction of barbituric acids mediated by KBr-H2O2 as a greener brominating reagent is described. The simple product workup, use of inexpensive greener reagent KBr-H2O2 for bromination and simple purification without column are the additional advantages of synthetic protocol.
- Zade, Mangesh N.,Katiya, Manish M.,Sontakke, Madhuri M.,Dhonde, Madhukar G.,Berad, Baliram N.,Thakare, Vijay J.,Bhaskar, Chandrakant S.
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p. 553 - 558
(2020/07/02)
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- Amberlyst-15 as a highly efficient and reusable catalyst for direct C-S bond formation: Synthesis of barbituryl carbamodithioates
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The C-S bond formation reaction has been described by the reaction of Bromo-barbituric acid with ammonium aryl dithiocarbamates in the presence of Amberlyst-15 as a reusable catalyst in aqueous medium. The mild reaction conditions, easy product isolation
- Sontakke, Madhuri M.,Bhaskar, Chandrakant S.,Berad, Baliram N.,Dhonde, Madhukar G.
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p. 115 - 121
(2015/06/22)
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- Monobromomalononitrile: An efficient regioselective mono brominating agent towards active methylene compounds and enamines under mild conditions
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The potential of monobromomalononitrile (MBM) as a convenient source of cationic bromine in organic bromination reaction has been explored. Studies reveal that MBM can be a good substitute for N-bromosuccinimide (NBS) in various respects. Enamines and act
- Pathak, Sudipta,Kundu, Ashis,Pramanik, Animesh
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p. 10180 - 10187
(2014/03/21)
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- C-S bond-forming reactions of barbiturylbromide with isothiocarbamides in aqueous media
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The C-S cross coupling of pharmaceutically active barbituric acid derivatives has been achieved by the interaction of selective monobromobarbituric acid with thioureas in an aqueous medium. This method is applicable for simple thiourea as well as monosubstituted thioureas, and corresponding products are obtained in good yield. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
- Sontakke, Madhuri M.,Jichkar, Atul A.,Dhonde, Madhukar G.,Bhaskar, Chandrakant S.,Berad, Baliram N.
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supporting information
p. 340 - 345
(2014/01/06)
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- Synthesis and evaluation of substituted 5-(3-chloro-2-oxo-4-phenylazetidin- 1-ylamino)pyrimidine-2,4,6(1H,3H,5H)-triones against pentylenetetrazole-induced convulsant in mice
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This study was designed to synthesis of substituted 5-(3-chloro-2-oxo-4- phenylazetidin-1-ylamino)pyrimidine-2,4,6(1H,3H,5H)-triones followed by evaluation against pentylenetetrazole-(PTZ) induced convulsant in mice. The titled compoundswere confirmed by
- Puri, Karan Deep Singh,Sood, Shailja,Muthuraman, Arunachalam
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p. 2300 - 2306,7
(2020/07/30)
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- Synthesis and?anticonvulsant activity of?some?potential thiazolidinonyl 2-oxo/thiobarbituric acids
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A series of 5-[(N-substituted benzylidenylimino)amino]-2-oxo/thiobarbituric acids (3a-3h) have been synthesized by the condensation of 5-hydrazino-2-oxo/thiobarbituric acids (2a-2b) with various aromatic aldehydes. Cycloaddition of thioglycolic acid to 3a
- Agarwal,Lata,Saxena,Srivastava,Kumar
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p. 1223 - 1229
(2007/10/03)
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- 5-Bromobarbituric acid : A mild and selective monobrominating agent employed in the synthesis of the gastrin antagonist GR174152
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5-Bromobarbituric acid (5) is a convenient reagent for the selective bromination of cyclic imine 3. A facile, in situ synthesis of this reagent involving a disproportionation reaction between barbituric acid and dibromobarbituric acid is described.
- Bright, Robert,Coote, Steven J.,Freeman, Stephen,Hayes, Doug,Smith, Gordon,Tapolczay, David
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p. 4195 - 4209
(2007/10/03)
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- The sonolysis of uracil
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The sonolysis of uracil (1) has been studied at 630 kHz in the presence of air, oxygen, nitrogen and argon.The degradation products were identified by gc-ms analysis.Under aerated conditions the following products were found: uracil glycols (7), isobarbituric acid (8), N-formyl-N'-glyoxylurea (6), 5-hydroxyhydantoin (9), dialuric acid (10), alloxan monohydrate (12), parabanic acid (13), and oxaluric acid (14).In deaerated solutions 6, 13, and 14 were not observed but either 6-hydroxy-5,6-dihydrouracil (17) or its isomer (18) were detected in addition to 7, 8, 9, 10, and 12.The observed products have been used to develop a possible mechanism for the sonolytic degradation and the results are similar to those obtained in radiolysis.The sonolytic degradation of 5-bromouracil (19) is also reported: the products observed were 5-bromobarbituric acid (20), 12, 13, 14, and 9 and these can be rationalized by a similar mechanism scheme.
- Yu, Tain-Jen,Sutherland, Ronald G.,Verrall, Ronald E.
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p. 1909 - 1915
(2007/10/02)
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