General approach to substituted naphtho[1,2-b]benzofurans via photochemical 6π-electrocyclization of benzofuranyl containing cinnamonitriles

Lichitsky, Boris V.; Karibov, Turan T.; Melekhina, Valeriya G.; Komogortsev, Andrey N.; Фахрутдинов, Артем Н.; Minyaev, Mikhail E.; Krayushkin, М. М.

doi:10.1016/j.tet.2021.132207

Cited by 10 publications

(10 citation statements)

References 43 publications

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“…At the same time, the benzofuran core was built on the basis of 3,4‐dimethoxyphenol, which was used earlier for the synthesis of similar benzene derivatives. [ 32 ]…”

Section: Resultsmentioning

confidence: 99%

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

Karibov

Lichitsky

Komogortsev

et al. 2022

Journal of Heterocyclic Chem

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The photochemical 6π‐electrocyclization of 1,3,5‐hexatriene system containing benzofuran and 2,5‐dichlorothiophene fragments was investigated. It was shown that considered photoreaction regiospecifically leads to the formation of substituted benzo[b]thieno[2,3‐g]benzofurans. Along with the formation of polyheterocyclic products the studied process is accompanied by the elimination of hydrogen chloride molecule. Based on the suggested transformation an efficient method for the photogeneration of strong acid was implemented. As a result, the starting thienyl substituted benzofurans can be used as photoacid generators (PAGs). The structure of one of the final products was established by X‐ray diffraction.

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“…At the same time, the benzofuran core was built on the basis of 3,4‐dimethoxyphenol, which was used earlier for the synthesis of similar benzene derivatives. [ 32 ]…”

Section: Resultsmentioning

confidence: 99%

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

Karibov

Lichitsky

Komogortsev

et al. 2022

Journal of Heterocyclic Chem

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“…A dark yellow colored precipitate indicated the completion of reaction. Solvent was removed and neutralized with HCl which was then extracted in ethyl acetate to account for compound (72). 72 and hydrazine hydrate were refluxed for three hours and poured into crushed ice after the completion of the reaction.…”

Section: Synthetic Strategies Of Benzofuran Derivativesmentioning

confidence: 99%

“…The methods and plausible mechanism is presented in Scheme 43, Scheme 44 and Scheme 45. [72 A new method involving acid and mild reaction conditions to synthesize regioselective trifluoromethylselenolated benzofurans (250) was developed by Liu and co-workers (Scheme 46). 2-phenylbenzofuran (248) was reacted with Se-(trifluoromethyl) 4-methylbenzenesulfonoselenoate (249) at 70 °C for 6 hours using ferric chloride as catalyst in DCE.…”

Section: Synthetic Strategies Of Benzofuran Derivativesmentioning

confidence: 99%

Advances in Synthetic Strategies and Medicinal Importance of Benzofurans: A Review

Dwarakanath

Gaonkar

2022

Asian J Org Chem

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Out of the many heterocycles that exhibit pharmaceutical and therapeutic properties, benzofurans remain the most eye-catching to scientists ever since their discovery. From being present in natural products to synthetic analogs they show diverse biological properties which are used to treat various diseases. Interestingly, some of the benzofuran hybrids were docked against COVID-19 Main Protease and it showed appealing results. Apart from medicinal properties it also exhibits some non-drug applications. The structure activity relationship of benzofuran derivatives in many infections draws attention to the extent where drugs can be produced in a short time span which highlights their significance in medicinal chemistry. There are considerable reaction schemes to synthesize this moiety either simple one pot reactions or multistep. Here, we emphasize on the chemistry of benzofurans, synthesis and its derivatives in the recent years, some of which show notable anti-tumor, antifungal, anti-mycobacterial and anti-oxidant activities.

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“…Ongoing our research in the area of UV-induced reactions of oxygen-containing heterocyclic systems, [24][25][26][27][28] for the first time herein, we described a novel efficient approach for the synthesis of 3a,6a-dihydroxy-4-methyl-2,3,3a,6a-tetrahydro-6Hcyclopenta[b]furan-6-one derivatives 11 based on photochemical transformation of allomaltols 12 containing an 2-aryl-2hydroxyethyl fragment (Scheme 1, D).…”

Section: Introductionmentioning

confidence: 99%

Photochemical Synthesis of Tetrahydro‐6H‐cyclopenta[b]furan‐6‐ones from Substituted Allomaltols

et al. 2022

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A novel UV‐mediated approach for the synthesis of previously unknown 3a,6a‐dihydroxy‐4‐methyl‐2,3,3a,6a‐tetrahydro‐6H‐cyclopenta[b]furan‐6‐one derivatives from easily accessible substituted allomaltols containing a 2‐aryl‐2‐hydroxyethyl fragment was elaborated. The suggested method is based on the ESIPT‐promoted contraction of a 3‐hydroxy‐4‐pyranone moiety followed by intramolecular trapping of a photogenerated α‐hydroxy‐1,2‐diketone intermediate. For the first time, we have demonstrated that a side chain hydroxyl group can be employed for the concluding cyclization with a labile α‐hydroxy‐1,2‐diketone fragment. The structure of one synthesized photoproduct was determined by X‐ray diffraction.

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General approach to substituted naphtho[1,2-b]benzofurans via photochemical 6π-electrocyclization of benzofuranyl containing cinnamonitriles

Cited by 10 publications

References 43 publications

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

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

Advances in Synthetic Strategies and Medicinal Importance of Benzofurans: A Review

Photochemical Synthesis of Tetrahydro‐6H‐cyclopenta[b]furan‐6‐ones from Substituted Allomaltols

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