Comparative Studies of Catalytic Application of Cerium(III)
Chloride and Resin Supported Cerium(III) in Domino Syntheses of
1,5-Benzodiazepine and 1,3-Diazine Skeletons

J 2014

Comparative Studies of Catalytic Application of Cerium(III) Chloride and Resin Supported Cerium(III) in Domino Syntheses of 1,5-Benzodiazepine and 1,3-Diazine Skeletons

HAVRÁNKOVÁ, Eva and Pavel PAZDERA

Basic information

Original name

Comparative Studies of Catalytic Application of Cerium(III) Chloride and Resin Supported Cerium(III) in Domino Syntheses of 1,5-Benzodiazepine and 1,3-Diazine Skeletons

Authors

HAVRÁNKOVÁ, Eva (203 Czech Republic, belonging to the institution) and Pavel PAZDERA (203 Czech Republic, guarantor, belonging to the institution)

Edition

Journal of Chemical Engineering and Chemistry Research, 2014, 2333-9195

Other information

Language

English

Type of outcome

Article in a journal

Field of Study

10401 Organic chemistry

Country of publisher

United States of America

Confidentiality degree

is not subject to a state or trade secret

References:

URL

RIV identification code

RIV/00216224:14310/14:00081737

Organization unit

Faculty of Science

Keywords in English

Dihydropyrimidinones; 1.5-Benzodiazepines; Metal Catalysis; Polymer Supported Ce(III); Solid Support Catalysis

Abstract

In the original language

We report on results of comparative studies of catalytic application of new green catalyst, i. e. cerium(III) supported on weekly acidic cation exchanger resin of polyacrylate typein view of the known catalysts based on cerium(III) chloride (free salt in the heptahydrate form eventually doped by sodium iodide or supported on silica gel) in domino syntheses of 2,3-dihydro-1H-1,5-benzodiazepines and 3,4-dihydropyrimidin-2(1H)-ones. Catalyzed domino synthesis of four model 2,3-dihydro-1H-1,5-benzodiazepines were carried out by the solvent free reaction of o-phenylenediamine with corresponding acyclic or cyclic ketone in molar ratio 1:2:2 at room temperature. Three selected 5-ethoxycarbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones were prepared in catalyzed domino three-component synthesis by reaction of ethyl acetoacetate, corresponding benzaldehyde and urea in molar ratio 1:1:3 under boiling in ethanol. The title products were obtained under studied catalytic conditions in very good yields and their identity was confirmed. It was found that the efficiency of the catalytic systems in the syntheses of title benzodiazepines depend on the electron effect of substituents present in the starting benzaldehydes. To confirm the capability of new catalytic system, the above mentioned domino syntheses were realized also without the catalyst but this setup led usually to worse results. Further, it was found that the cerium(III) cation supported on the resin proved to be at least as effective as other used catalytic systems and it is inexpensive, stable, can be easily recycled and reused. Finally, application of cerium(III) supported on low-cost industrial resin further increases green impact of studied domino syntheses for the both title compound class.

Links

2A-1TP1/090, research and development project

Name: Nové katalyzátory a činidla pro udržitelné zelené syntézy a kombinatoriální syntézy.

Investor: Ministry of Industry and Trade of the CR, New catalysts and reagents for sustainable green syntheses and combinatorial syntheses

Cite

HAVRÁNKOVÁ, Eva and Pavel PAZDERA. Comparative Studies of Catalytic Application of Cerium(III) Chloride and Resin Supported Cerium(III) in Domino Syntheses of 1,5-Benzodiazepine and 1,3-Diazine Skeletons. Journal of Chemical Engineering and Chemistry Research. 2014, vol. 2014, No 10, p. 229-237. ISSN 2333-9195.

@article{1301133,
   author = {Havránková, Eva and Pazdera, Pavel},
   article_number = {10},
   keywords = {Dihydropyrimidinones; 1.5-Benzodiazepines; Metal Catalysis; Polymer Supported Ce(III); Solid Support Catalysis},
   language = {eng},
   issn = {2333-9195},
   journal = {Journal of Chemical Engineering and Chemistry Research},
   title = {Comparative Studies of Catalytic Application of Cerium(III) Chloride and Resin Supported Cerium(III) in Domino Syntheses of 1,5-Benzodiazepine and 1,3-Diazine Skeletons},
   url = {https://www.researchgate.net/publication/267390365_Comparative_Studies_of_Catalytic_Application_of_Cerium%28III%29_Chloride_and_Resin_Supported_Cerium%28III%29_in_Domino_Syntheses_of_15-Benzodiazepine_and_13-Diazine_Skeletons},
   volume = {2014},
   year = {2014}
}

TY  - JOUR
ID  - 1301133
AU  - Havránková, Eva - Pazdera, Pavel
PY  - 2014
TI  - Comparative Studies of Catalytic Application of Cerium(III) Chloride and Resin Supported Cerium(III) in Domino Syntheses of 1,5-Benzodiazepine and 1,3-Diazine Skeletons
JF  - Journal of Chemical Engineering and Chemistry Research
VL  - 2014
IS  - 10
SP  - 229-237
EP  - 229-237
SN  - 23339195
KW  - Dihydropyrimidinones
KW  - 1.5-Benzodiazepines
KW  - Metal Catalysis
KW  - Polymer Supported Ce(III)
KW  - Solid Support Catalysis
UR  - https://www.researchgate.net/publication/267390365_Comparative_Studies_of_Catalytic_Application_of_Cerium%28III%29_Chloride_and_Resin_Supported_Cerium%28III%29_in_Domino_Syntheses_of_15-Benzodiazepine_and_13-Diazine_Skeletons
L2  - https://www.researchgate.net/publication/267390365_Comparative_Studies_of_Catalytic_Application_of_Cerium%28III%29_Chloride_and_Resin_Supported_Cerium%28III%29_in_Domino_Syntheses_of_15-Benzodiazepine_and_13-Diazine_Skeletons
N2  - We report on results of comparative studies of catalytic application of new green catalyst, i. e. cerium(III) supported on weekly acidic cation exchanger resin of polyacrylate typein view of the known catalysts based on cerium(III) chloride (free salt in the heptahydrate form eventually doped by sodium iodide or supported on silica gel) in domino syntheses of 2,3-dihydro-1H-1,5-benzodiazepines and 3,4-dihydropyrimidin-2(1H)-ones. Catalyzed domino synthesis of four model 2,3-dihydro-1H-1,5-benzodiazepines were carried out by the solvent free reaction of o-phenylenediamine with corresponding acyclic or cyclic ketone in molar ratio 1:2:2 at room temperature. Three selected 5-ethoxycarbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones were prepared in catalyzed domino three-component synthesis by reaction of ethyl acetoacetate, corresponding benzaldehyde and urea in molar ratio 1:1:3 under boiling in ethanol. The title products were obtained under studied catalytic conditions in very good yields and their identity was confirmed. It was found that the efficiency of the catalytic systems in the syntheses of title benzodiazepines depend on the electron effect of substituents present in the starting benzaldehydes. To confirm the capability of new catalytic system, the above mentioned domino syntheses were realized also without the catalyst but this setup led usually to worse results. Further, it was found that the cerium(III) cation supported on the resin proved to be at least as effective as other used catalytic systems and it is inexpensive, stable, can be easily recycled and reused. Finally, application of cerium(III) supported on low-cost industrial resin further increases green impact of studied domino syntheses for the both title compound class.
ER  -

HAVRÁNKOVÁ, Eva and Pavel PAZDERA. Comparative Studies of Catalytic Application of Cerium(III) Chloride and Resin Supported Cerium(III) in Domino Syntheses of 1,5-Benzodiazepine and 1,3-Diazine Skeletons. \textit{Journal of Chemical Engineering and Chemistry Research}. 2014, vol.~2014, No~10, p.~229-237. ISSN~2333-9195.

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