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Vol. 26 No. 18 (2014): Vol 26 Issue 18

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Design and Synthesis of Three Naphthol Derivatives Using Several Strategies

https://doi.org/10.14233/ajchem.2014.16448
Lauro Figueroa-Valverde
Laboratory of Pharmaco-Chemistry, Faculty of Chemical Biological Sciences, University Autonomous of Campeche, Av. Agustín Melgar s/n, Col Buenavista C.P. 24039 Campeche Cam., México
Francisco Diaz-Cedillo
Escuela Nacional de Ciencias Biológicas del Instituto Politécnico Nacional. Prol. Carpio y Plan de Ayala s/n Col. Santo Tomas, México, D.F. C.P. 11340, Mexico
Marcela Rosas-Nexticapa
Facultad de Nutrición, Universidad Veracruzana, Médicos y Odontologos s/n C.P. 91010, Unidad del Bosque Xalapa Veracruz, México
Elodia Garcia-Cervera
Laboratory of Pharmaco-Chemistry, Faculty of Chemical Biological Sciences, University Autonomous of Campeche, Av. Agustín Melgar s/n, Col Buenavista C.P. 24039 Campeche Cam., México
Eduardo Pool-Gomez
Laboratory of Pharmaco-Chemistry, Faculty of Chemical Biological Sciences, University Autonomous of Campeche, Av. Agustín Melgar s/n, Col Buenavista C.P. 24039 Campeche Cam., México
Maria Lopez-Ramos
Laboratory of Pharmaco-Chemistry, Faculty of Chemical Biological Sciences, University Autonomous of Campeche, Av. Agustín Melgar s/n, Col Buenavista C.P. 24039 Campeche Cam., México

Corresponding Author(s) : Lauro Figueroa-Valverde

lauro_1999@yahoo.com

Asian Journal of Chemistry, Vol. 26 No. 18 (2014): Vol 26 Issue 18

Abstract

In this study, three naphthol derivatives were synthesized. The first stage, involved preparation of 3-[[2-(3-hydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclo-penta[a]phenanthren-17-ylideneamino)-ethylamino]-(3-hydroxy-naphtalen-2-yl)-methyl]-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one (4) by the reaction of 1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one (1) with 17-(2-amino-ethylimino)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-ol (2) and 2-hydroxy-1-naphthaldehyde (3) using proline as catalyst. The second stage was achieved by the reaction of compund 1 with 1-[(2-amino-ethylamino)-phenyl-methyl]-naphthalen-2-ol to form the compound 1-{phenyl-[2-(1,7,7-trimethylbicyclo[2.2.1]hept-2-ylideneamino)ethyl-amino]-methyl}naphtalen-2-ol (6) using boric acid as catalyst. The third stage was achieved by the synthesis of N-[3-(1-hydroxy-10a,12a-dimethyl-2,2,3a,3b,4,5,10,10a,10b,11,12,12a-dodecahydro-1H-7-oxa-8-azadicyclopenta[a,h]phenanthren-1-ylethynylamino)-3-(3-hydroxy-naphtalen-2-yl)-propyl]-succinamic acid 3-allyl-5-methoxy-phenylester (9) using the three components system (2-hydroxy-1-naphthaldehyde, 4-allyl-2-methoxyphenyl 4-[(2-aminoethyl)amino]-4-oxobutanoate anddanazol). The structure of all compounds obtained was confirmed by elemental analysis, spectroscopy and spectrometry data.

Keywords

Naphthol derivative Boric acid Proline
Figueroa-Valverde, L., Diaz-Cedillo, F., Rosas-Nexticapa, M., Garcia-Cervera, E., Pool-Gomez, E., & Lopez-Ramos, M. (2014). Design and Synthesis of Three Naphthol Derivatives Using Several Strategies. Asian Journal of Chemistry, 26(18), 6001–6004. https://doi.org/10.14233/ajchem.2014.16448
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