An Approach to the Synthesis of 1-Propenylnaphthols and 3-Arylnaphtho[2,1-b]furans

Abstract

A simple and efficient strategy for the synthesis of 1-propenylnaphthols from readily accessible 3-arylallylnaphthyl ethers has been developed. By using KCO as base and 2-methoxyethanol as solvent, direct access to a wide range of 1-propenylnaphthols can be achieved in generally good yield (up to 99%) with high stereoselectivity toward the Z isomer. The control experiments indicate that the reaction proceeds through a sequential Claisen rearrangement/isomerization process. Furthermore, starting from the same material, the highly valuable 3-arylnaphtho[2,1-b]furans can be obtained in N,N-dimethylformamide and in the presence of AgO as the oxidant via a one-pot sequential Claisen rearrangement/isomerization/cyclization reaction. Mechanistic studies confirm that 1-propenylnaphthols are the key intermediates to form the 3-arylnaphtho[2,1-b]furans. In addition, these two operationally simple and practical protocols could be scaled up to a gram level.

Synthesis of Polyaryl-Substituted Olefins via a Rh(III)-Catalyzed One-Pot Reaction Using N-Phenoxyacetamides, Ketones, and Hydrazines

“…Since the olefin and the phenol units in these products offer additional synthetic opportunities. For example, either diaryl-substituted olefin 5k or triaryl-substituted ethylene 4f could convert to 2,3-disubstituted benzofurans 8 and 9 at high temperatures using Ag 2 O as an oxidant . The saturated biphenyl molecule 10 could be prepared by reduction in the presence of Pd/C (10%) with an excellent yield.…”

New Zampanolide Mimics: Design, Synthesis, and Antiproliferative Evaluation

“…Compound (E)-ethyl 3-(2-fluorophenyl)acrylate was synthesized by the Wittig reaction of the commercially available 2-fluorobenzaldehyde (10) with ethyl 2-(triphenyl-phosphoranylidene)acetate (11) according to the procedure described in the literature [26]. (E)-3-(2-Fluorophenyl)prop-2-en-1-ol (13) was synthesized by reducing (E)-ethyl 3-(2-fluorophenyl)acrylate (12) with diisobutylaluminium hydride (DIBAL) based on the procedure reported in the literature [27]. The Sharpless asymmetric dihydroxylation of the allylic alcohol (13) with AD-mix-α or AD-mix-β was performed following the standard experimental procedure reported in the literature and sulfonamide was used to accelerate the hydrolysis of osmate ester [25].…”

“…(E)-ethyl 3-(2-fluorophenyl)acrylate (12) was prepared from commercially available 2-fluorobenzaldehyde (10, CAS 446-52-6) according to the reported procedure [26]. (E)-3-(2-Fluorophenyl)prop-2-en-1-ol (13) was synthesized by reducing (E)-ethyl 3-(2-fluorophenyl)acrylate (12) with DIBAL based on the procedure reported in the literature [27]. Its structure was confirmed by 1 H NMR and high resolution mass spectrometry (HRMS) data (calculated for C 9 H 10 FO (M + H): 153.0716; Found: 153.0710).…”