Design and synthesis of three naphthol derivatives using several strategies

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-trimethyl-bicyclo[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,11,12,12adodecahydro-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.