Design and Synthesis of Two Chrysene Derivatives Using Estrone and Androsterone as Chemical Tools

Title:Design and Synthesis of Two Chrysene Derivatives Using Estrone and Androsterone as Chemical Tools

Volume: 13 Issue: 4

Author(s): Lauro Figueroa-Valverde, Francisco Díaz-Cedillo, Lenin Hau-Heredia, Marcela Rosas-Nexticapa, Benjamin Otto-Ortega, Elodia García-Cervera, Eduardo Pool-Gómez and María López-Ramos

Affiliation:

Keywords: Allyl alcohol, androsterone, crysene, estrone, isoquinoline.

Abstract: 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.

Cite this article as:

Figueroa-Valverde Lauro, Díaz-Cedillo Francisco, Hau-Heredia Lenin, Rosas-Nexticapa Marcela, Otto-Ortega Benjamin, García-Cervera Elodia, Pool-Gómez Eduardo and López-Ramos María, Design and Synthesis of Two Chrysene Derivatives Using Estrone and Androsterone as Chemical Tools, Letters in Organic Chemistry 2016; 13 (4) . https://dx.doi.org/10.2174/1570178613666160128232738