Design and synthesis of two chrysene derivatives using estrone and androsterone as chemical tools

Lauro Figueroa-Valverde, Francisco Diaz-Cedillo, Lenin Hau-Heredia, Marcela Rosas-Nexticapa, Benjamin Otto-Ortega, Elodia Garcia-Cervera, Eduardo Pool-Gomez, Maria Lopez-Ramos

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Abstract

© 2016 Bentham Science Publishers. Background: Several crysene derivatives have been prepared using different protocols; however some require special reagents and conditions. The aim of study involved the synthesis of two crysene,derivative using androsterone and estrone as chemical tool. Methods: Crysene derivatives were prepared by a series of reactions that involve; 1) Synthesis of two isoquinolinone derivatives by reaction of androsterone or estrone with p-nitrobenzoyl azide using imidazole as catalyst; 2) Reaction of the isoquinoline derivatives with ethylenediamine to form two chrysenol using boric acid as catalyst; 3) Synthesis of chrysene-carbaldehyde derivatives via oxidation of hydroxyl groups from chrysenol derivatives with DMSO; 4) Reaction of chrysene-carbaldehyde derivatives with phenylpropanone to form two chrysene-phenylpropenone analogs; 5) Preparation of chrisene-allylic alcohol derivatives by reaction of chrysene-phenylpropenones with benzaldehyde using imidazole as catalyst; 6) Synthesis of two chrisene-dione derivatives through oxidation of chrisene-allylic alcohols with DMSO; 7) Reaction of the chrisene-diones with ethylenediamine for preparation of two diazepin-chrisene derivatives using boric acid as catalyst. The chemical structure of compounds was determined by spectroscopic and spectrometric methods. Results: The 1H NMR spectrum for the chrysene derivatives showed signals at 4.50-4.76 ppm for azepine rings and at 6.50 and 7.46-8.36 ppm for phenyl groups. Conclusion: In conclusion, in this work were prepared two crysene derivatives using several chemical techniques, which are simple procedures and very ease of workup.
Original languageAmerican English
Pages (from-to)237-248
Number of pages212
JournalLetters in Organic Chemistry
DOIs
StatePublished - 1 May 2016

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Androsterone
Estrone
ethylenediamine
Derivatives
Dimethyl Sulfoxide
Azepines
Azides
Hydroxyl Radical
Catalysts
chrysene
Oxidation

Cite this

Figueroa-Valverde, L., Diaz-Cedillo, F., Hau-Heredia, L., Rosas-Nexticapa, M., Otto-Ortega, B., Garcia-Cervera, E., ... Lopez-Ramos, M. (2016). Design and synthesis of two chrysene derivatives using estrone and androsterone as chemical tools. Letters in Organic Chemistry, 237-248. https://doi.org/10.2174/1570178613666160128232738
Figueroa-Valverde, Lauro ; Diaz-Cedillo, Francisco ; Hau-Heredia, Lenin ; Rosas-Nexticapa, Marcela ; Otto-Ortega, Benjamin ; Garcia-Cervera, Elodia ; Pool-Gomez, Eduardo ; Lopez-Ramos, Maria. / Design and synthesis of two chrysene derivatives using estrone and androsterone as chemical tools. In: Letters in Organic Chemistry. 2016 ; pp. 237-248.
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abstract = "{\circledC} 2016 Bentham Science Publishers. Background: Several crysene derivatives have been prepared using different protocols; however some require special reagents and conditions. The aim of study involved the synthesis of two crysene,derivative using androsterone and estrone as chemical tool. Methods: Crysene derivatives were prepared by a series of reactions that involve; 1) Synthesis of two isoquinolinone derivatives by reaction of androsterone or estrone with p-nitrobenzoyl azide using imidazole as catalyst; 2) Reaction of the isoquinoline derivatives with ethylenediamine to form two chrysenol using boric acid as catalyst; 3) Synthesis of chrysene-carbaldehyde derivatives via oxidation of hydroxyl groups from chrysenol derivatives with DMSO; 4) Reaction of chrysene-carbaldehyde derivatives with phenylpropanone to form two chrysene-phenylpropenone analogs; 5) Preparation of chrisene-allylic alcohol derivatives by reaction of chrysene-phenylpropenones with benzaldehyde using imidazole as catalyst; 6) Synthesis of two chrisene-dione derivatives through oxidation of chrisene-allylic alcohols with DMSO; 7) Reaction of the chrisene-diones with ethylenediamine for preparation of two diazepin-chrisene derivatives using boric acid as catalyst. The chemical structure of compounds was determined by spectroscopic and spectrometric methods. Results: The 1H NMR spectrum for the chrysene derivatives showed signals at 4.50-4.76 ppm for azepine rings and at 6.50 and 7.46-8.36 ppm for phenyl groups. Conclusion: In conclusion, in this work were prepared two crysene derivatives using several chemical techniques, which are simple procedures and very ease of workup.",
author = "Lauro Figueroa-Valverde and Francisco Diaz-Cedillo and Lenin Hau-Heredia and Marcela Rosas-Nexticapa and Benjamin Otto-Ortega and Elodia Garcia-Cervera and Eduardo Pool-Gomez and Maria Lopez-Ramos",
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Figueroa-Valverde, L, Diaz-Cedillo, F, Hau-Heredia, L, Rosas-Nexticapa, M, Otto-Ortega, B, Garcia-Cervera, E, Pool-Gomez, E & Lopez-Ramos, M 2016, 'Design and synthesis of two chrysene derivatives using estrone and androsterone as chemical tools', Letters in Organic Chemistry, pp. 237-248. https://doi.org/10.2174/1570178613666160128232738

Design and synthesis of two chrysene derivatives using estrone and androsterone as chemical tools. / Figueroa-Valverde, Lauro; Diaz-Cedillo, Francisco; Hau-Heredia, Lenin; Rosas-Nexticapa, Marcela; Otto-Ortega, Benjamin; Garcia-Cervera, Elodia; Pool-Gomez, Eduardo; Lopez-Ramos, Maria.

In: Letters in Organic Chemistry, 01.05.2016, p. 237-248.

Research output: Contribution to journalArticle

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T1 - Design and synthesis of two chrysene derivatives using estrone and androsterone as chemical tools

AU - Figueroa-Valverde, Lauro

AU - Diaz-Cedillo, Francisco

AU - Hau-Heredia, Lenin

AU - Rosas-Nexticapa, Marcela

AU - Otto-Ortega, Benjamin

AU - Garcia-Cervera, Elodia

AU - Pool-Gomez, Eduardo

AU - Lopez-Ramos, Maria

PY - 2016/5/1

Y1 - 2016/5/1

N2 - © 2016 Bentham Science Publishers. Background: Several crysene derivatives have been prepared using different protocols; however some require special reagents and conditions. The aim of study involved the synthesis of two crysene,derivative using androsterone and estrone as chemical tool. Methods: Crysene derivatives were prepared by a series of reactions that involve; 1) Synthesis of two isoquinolinone derivatives by reaction of androsterone or estrone with p-nitrobenzoyl azide using imidazole as catalyst; 2) Reaction of the isoquinoline derivatives with ethylenediamine to form two chrysenol using boric acid as catalyst; 3) Synthesis of chrysene-carbaldehyde derivatives via oxidation of hydroxyl groups from chrysenol derivatives with DMSO; 4) Reaction of chrysene-carbaldehyde derivatives with phenylpropanone to form two chrysene-phenylpropenone analogs; 5) Preparation of chrisene-allylic alcohol derivatives by reaction of chrysene-phenylpropenones with benzaldehyde using imidazole as catalyst; 6) Synthesis of two chrisene-dione derivatives through oxidation of chrisene-allylic alcohols with DMSO; 7) Reaction of the chrisene-diones with ethylenediamine for preparation of two diazepin-chrisene derivatives using boric acid as catalyst. The chemical structure of compounds was determined by spectroscopic and spectrometric methods. Results: The 1H NMR spectrum for the chrysene derivatives showed signals at 4.50-4.76 ppm for azepine rings and at 6.50 and 7.46-8.36 ppm for phenyl groups. Conclusion: In conclusion, in this work were prepared two crysene derivatives using several chemical techniques, which are simple procedures and very ease of workup.

AB - © 2016 Bentham Science Publishers. Background: Several crysene derivatives have been prepared using different protocols; however some require special reagents and conditions. The aim of study involved the synthesis of two crysene,derivative using androsterone and estrone as chemical tool. Methods: Crysene derivatives were prepared by a series of reactions that involve; 1) Synthesis of two isoquinolinone derivatives by reaction of androsterone or estrone with p-nitrobenzoyl azide using imidazole as catalyst; 2) Reaction of the isoquinoline derivatives with ethylenediamine to form two chrysenol using boric acid as catalyst; 3) Synthesis of chrysene-carbaldehyde derivatives via oxidation of hydroxyl groups from chrysenol derivatives with DMSO; 4) Reaction of chrysene-carbaldehyde derivatives with phenylpropanone to form two chrysene-phenylpropenone analogs; 5) Preparation of chrisene-allylic alcohol derivatives by reaction of chrysene-phenylpropenones with benzaldehyde using imidazole as catalyst; 6) Synthesis of two chrisene-dione derivatives through oxidation of chrisene-allylic alcohols with DMSO; 7) Reaction of the chrisene-diones with ethylenediamine for preparation of two diazepin-chrisene derivatives using boric acid as catalyst. The chemical structure of compounds was determined by spectroscopic and spectrometric methods. Results: The 1H NMR spectrum for the chrysene derivatives showed signals at 4.50-4.76 ppm for azepine rings and at 6.50 and 7.46-8.36 ppm for phenyl groups. Conclusion: In conclusion, in this work were prepared two crysene derivatives using several chemical techniques, which are simple procedures and very ease of workup.

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