2-(2-(4-Methoxyphenyl)-4,9-dimethyl-7-oxo-7H-furo[2,3-f]chromen-3-yl)acetic Acid

Abstract

For the first time, we describe a new approach towards the synthesis of previously unknown 2-(2-(4-methoxyphenyl)-4,9-dimethyl-7-oxo-7H-furo[2,3-f]chromen-3-yl)acetic acid. The presented method is based on the multicomponent condensation of 5-hydroxy-4,7-dimethyl-2H-chromen-2-one, 4-methoxyphenylglyoxal and Meldrum’s acid. It was shown that the studied reaction proceeds in two steps including the initial interaction of starting materials in MeCN and the final formation of furylacetic acid moiety in acidic media. The structures of the obtained compound were established by 1H, 13C-NMR spectroscopy and high-resolution mass spectrometry.

2-(5-Acetyl-7-methoxy-2-(4-methoxyphenyl)benzofuran-3-yl)acetic Acid

“…It should be mentioned that the final step of the reaction involves intramolecular cyclization in a mixture of hydrochloric and acetic acids. As was shown previously, these conditions are optimal for the last stage of the process [18][19][20][21][22][23][24]. Thus, the presented approach allows one to obtain the target product 4 in a 62% yield.…”

“…Previously, we proposed a general method for the preparation of condensed furylacetic acids based on a multicomponent reaction of hydroxyl derivatives with arylglyoxals and Meldrum's acid [18][19][20][21][22][23][24]. It should be noted that the considered method allows one to synthesize the wide range of furylacetic acids from the diverse phenols.…”

Photoinduced 6π‐electrocyclization of 2,5‐dichlorothiophene containing benzofuranylacrylonitriles as efficient method for the generation of hydrogen chloride

“…Furthermore, as a result of UV-induced cyclization, a polycyclic product 4q is formed simultaneously with the photogeneration of a hydrogen chloride molecule (Scheme 4). Thus, taking into account the synthetic availability and diversity of 2-arylfuryl-3-acetic acids, [41][42][43][44][45][46][47][48] the proposed approach open access to a wide range of photoacid generators of this type.…”

Recent Advances on Sustainable Synthesis of Furocoumarins

“…In 2021, Lichitsky and his group reported a one‐pot multicomponent reaction for the synthesis of furocoumarin derivatives from the reaction of 5‐hydroxy‐4,7‐dimethyl‐2Hchromen‐2‐one with 4‐methoxyphenylglyoxal and Meldrum's acid by using Et 3 N as base ( Scheme 44). [84] Instead of using chromatographic separation, the product can be obtained simply by filtration. However, due to the low reactivity of 5‐hydroxy coumarin, this reaction required a long reflux time (16 h) to improve the conversion of the starting materials.…”