- Synthesis, photophysical studies, solvatochromic analysis and TDDFT calculations of diazaspiro compounds
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Diazaspiro[5.5]undecane-1,3,5,9-tetraones and 3-thioxo-diazaspiro[5.5]undecane-1,5,9-trione have been synthesized via double Michael addition of 1,5-diphenyl-1,4-pentadien-3-one with active methylene heterocycles N,N-dimethyl barbituric acid, barbituric a
- Aggarwal, Komal,Khurana, Jitender M.
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p. 288 - 297
(2015/03/18)
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- New spiro (thio) barbiturates based on cyclohexanone and bicyclo [3.1.1]heptan-6-one by nonconcerted [1+5] cyclo addition reaction and their conformational structures
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Crossed-aldol condensation reaction of aromatic aldehydes with ketones such as; acetone and cyclohexanone leads to the efficient formation of cross conjugated α,β-unsaturated ketones in excellent yield. The intermolecular and then intramolecular Michael addition reaction of α,β-unsaturated ketones derived from acetone and cyclohexanone with (thio)barbituric acids lead to synthesis new type of 7,11-diaryl-2,4-diazaspiro[5.5]undecane-1,3,5,9-tetraone and 2,4-diaryl-1'H-spiro[bicyclo[3.3.l]nonane-3,5'-pyrimidine]-2',4',6',9(3'H)-tetraone, respectively in good yield. Structure elucidation is carried out by 1H NMR, 13C NMR, FT-IR, UV-Visible, mass spectroscopy and X-ray crystallography techniques. A possible mechanism of the formation is discussed. The structural conformation also demonstrated by coupling constants derived from dihedral angles between vicinal and geminal protons. The 1H NMR spectra of NH protons of spiro compounds derived from barbituric acid show a broad singlet peak instead, these protons in the spiro compounds derived from thiobarbituric acid show two distinct peaks.
- Pesyan, Nader Noroozi,Noori, Sirons,Poorhassan, Soodabeh,ahin, Ertan
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p. 423 - 440
(2015/02/02)
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- 7,11-diaryl-2,4-diazaspiro[5.5]undecane-1,5,9-triones: A new series of spiroheterocycles
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A novel two step synthesis of 7,11-diaryl-2,4-diazaspiro[5.5]undecane-1,5,9-triones has been reported based on double Michael addition of 2-thiobarbiturates or N,N'-diaryl-2-thiobarbiturates with dibenzalacetones followed by reductive desulfurization with
- Khurana, Jitender M.,Arora, Reema,Satija, Sarishti
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p. 2709 - 2716
(2008/09/19)
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- Studies on spiroheterocycles, Part II: Heterocyclization of the spiro compounds containing cyclohexanone and thiobarbituric acid with different bidentate nucleophilic reagents
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The reaction of thiobarbituric acid with different diarylidene ketones 1a-c yields the spiro compounds 2a-c. The diarylidene derivatives 3a-c are synthesized by the condensation of spiro compounds 2a-c with different aldehydes. A series of spiro heterocyc
- Behera, Rajani Kanta,Behera, Ajay Kumar,Pradhan, Rosy,Pati, Anita,Patra, Manabendra
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p. 3729 - 3742
(2007/10/03)
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- Synthesis and anticonvulsant activity of some spiro compounds derived from barbituric and thiobarbituric acids: Part I
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Divinyl ketones (1), prepared by the condensation of acetone with the appropriate aromatic aldehydes, on Michael addition with barbituric and thiobarbituric acids afford the desired spiro compounds (2a-j). The ketoximes (3a-j) obtained from 2a-j on Beckmann transformation by treatment with PCl5 furnish the spiro azepines (4a-j). Alkylation of some of the compounds 2 afford the anticipated N-substituted products (5a-i). Preliminary pharmacological screening of some of the new compounds reveal their anticonvulsant activity.
- Osman,Kandeel,Said,Ahmed
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p. 1073 - 1078
(2007/10/03)
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