Synthesis of neoflavonoids: 4-(4’-methoxyphenyl)-3,4-dihydrocoumarins

Abstract

hidrogenado. Os produtos das reações foram caracterizados com base nos da dos espectrais de RMN 1 H e 13 C, usando-se principalmente a técnica de espectroscopia nOe diferencial.The neoflavonoids 7-hydroxy-5-methyl-4-(4'-methoxyphenyl)-3,4-dihydrocumarin ( 1), 5-hydroxy-7-methyl-4-(4'-methoxyphenyl)-3,4-dihydrocoumarin ( 2), 5-methyl-7-O -coumaroyl-4-(4'-methoxyphenyl)-3,4-dihydrocoumarin ( 3), 5-hydroxy-4-(4'-methoxyphenyl)-α-pirano-(6",5":7,8)-3,4-dihydrocoumarin ( 7), and 7-pentadecyl-4-(4'-methoxyphenyl)-3,4-dihydrocoumarin ( 8) were syn the sized via the AlCl 3-cat a lyzed con den sa tion of 4-methoxycinnamic acid chlo ride with orcinol, 5,7-dihydroxycoumarin and hy dro ge nated cardanol. The com pounds were char ac ter ized on the ba sis of their 1 H-and 13 C-NMR spec tro scopic prop er ties, in clud ing nOe dif fer ence spectros copy.

One-Pot Synthesis of Cardanol-Derived High-Efficiency Antioxidants Based on Intramolecular Synergism

“…In 13 C NMR spectra, peaks appeared at 42.15, 41.37, and 47.66 ppm, corresponding to BA1, BA2, and BA3, respectively, were attributed to the Mannich bridge (Ar–CH 2 –NH) carbon. Furthermore, new peaks between 112.13 and 157.30 ppm also supported the formation of a phenol-aromatic amine structure …”

“…Furthermore, new peaks between 112.13 and 157.30 ppm also supported the formation of a phenol-aromatic amine structure. 33 HRMS. The structures of the biobased phenol-arylamine antioxidants were also characterized by the HRMS spectra presented in Figure 3 FT-IR Characterization.…”

Syntheses and Biological Activities of Chroman-2-ones. A Review

“…170 The first reported synthetic route for tolterodine tartrate (muscarine receptor antagonist used in the treatment of urinary bladder disorders) involved the acid-catalyzed reaction of cinnamic acid and 4-methylphenol 181 in sulfuric acid to give dihydrocoumarin derivative 28; this was followed by ring opening of the lactone to give a methyl ester, which was reduced to an alcohol using LAH. Tosylation of the resultant alcohol, followed by condensation of the tosyl derivative with diisopropylamine, yielded a tertiary amine, which on treatment with BBr 3 gave phenol 30 (Scheme 47a).…”

Single-step synthesis of 4-phenyl and 3,4-dihydro-4-phenyl coumarins using a recyclable Preyssler heteropolyacid catalyst under solvent-free reaction conditions

“…The methods for the synthesis of 4-phenyl-3,4-dihydrocoumarins include the catalytic hydrogenation of coumarins [24][25][26], the Pondorff reaction for the condensation of phenols with a, b-unsaturated acids in the presence of an acid catalyst (for example, H 2 SO 4 [17], P 2 O 5 /H 3 PO 4 H 3 [27], TFA [28], BF 3 [29], zeolites [30], and montmorillonite K-10 using microwave irradiation [22]), arylacrylate lactonization [20,[31][32][33], Houben-Hoesch condensation of phenols with a,b-unsaturated nitriles in the presence of ZnCl 2 [17] or AlCl 3 /HCl [34], consecutive Friedel-Crafts alkylation-acylation [35], and via Fischer carbenes [36].…”