取代苯并[b]呋喃衍生物的合成研究进展

doi:10.6023/cjoc202110008

摘要/Abstract

许多天然产物和具有生物活性的化合物中均含有苯并[b]呋喃结构. 苯并[b]呋喃衍生物具有抗病毒、抗癌、杀虫、抗炎镇痛和抗氧化等生物活性, 因而受到了药物化学工作者的青睐, 并且成为近年来有机合成研究的热点领域之一. 目前已有许多有效的合成方法被报道. 综述了近十年来, 在过渡金属催化及无催化剂的条件下, 通过环化或偶联反应制备取代苯并[b]呋喃衍生物的合成研究进展.

关键词: 苯并[b]呋喃, 偶联反应, 环化反应, 金属催化, 无催化剂, 研究进展

Benzo[b]furan structure is found in many natural products and bioactive compounds. Benzo[b]furan derivatives have attracted the attention of pharmaceutical chemists because of their antiviral, anticancer, insecticidal and anti inflammatory, analgesic and antioxidant activities. At present, many effective synthetic methods have been reported and become one of the hot topics of organic synthesis research in recent years. The research progress in the synthesis of substituted benzo[b]furan derivatives by cyclization or coupling reaction under the conditions of transition metal catalysis and catalysts free in recent ten years is reviewed.

Key words: benzo[b]furan, cross-coupling reaction, cyclization reaction, metal catalyst, catalyst free, research progress

引用此文

张志豪, 姜芯, 李清寒. 取代苯并[b]呋喃衍生物的合成研究进展[J]. 有机化学, 2022, 42(4): 945-964.

Zhihao Zhang, Xin Jiang, Qinghan Li. Recent Progress in the Synthesis of Substituted Benzo[b]furan Derivatives[J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 945-964.

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图/表 31

图式1. 钯催化烯丙基酯与邻羟基卤苯反应制备取代苯并[b]呋喃的可能机理

Scheme 1. Plausible mechanism of palladium catalyzed reaction of allylic esters with o-hydroxyhalobenzene to prepare substituted benzo[b]furans

图式2. 钯催化2-(1,1-二溴乙烯基)酚与苯基(三烷氧基)硅烷反应制备取代苯并[b]呋喃衍生物的可能机理

Scheme 2. Plausible mechanism of reaction of 2-(1,1-dibromo- vinyl)phenol with phenyl(trialkoxy)silane to prepare substituted benzo[b]furan derivatives catalyzed by palladium

图式3. 钯催化苯酚衍生物氧化环化反应制备苯并[b]呋喃衍生物的可能机理

Scheme 3. Plausible mechanism of oxidative cyclization of phenol derivatives to prepare benzo[b]furan derivatives catalyzed by palladium

图式4. 钯催化邻氯苯酚和末端炔烃环化反应制备取代苯并[b]呋喃衍生物的可能机理

Scheme 4. Plausible mechanism of cyclization of o-chlorophenol and terminal alkynes to benzo[b]furan derivatives catalyzed by palladium

图式5. 三环结构的苯并[b]呋喃衍生物的合成

Scheme 5. Synthesis of benzo[b]furan derivatives with tricyclic structure

图式6. 铜催化2-(2,2-二溴乙烯基)苯酚和苯乙炔环化反应制备取代苯并[b]呋喃衍生物的可能机制

Scheme 6. Plausible mechanism of copper catalyzed cyclization of 2-(2,2-dibromovinyl)phenol with phenylacetylene to prepare substituted benzo[b]furan derivatives

图式7. 铜催化酰氯、膦叶立德试剂和邻碘苯酚一锅法合成取代苯并[b]呋喃衍生物的可能机理

Scheme 7. Plausible mechanism of one-pot synthesis of substituted benzo[b]furan derivatives from acyl chloride, phosphine ylide reagent and o-iodophenol catalyzed by copper

图式8. 电石合成苯并[b]呋喃环的可能机理

Scheme 8. Possible mechanism of synthesis of benzo[b]furan rings from calcium carbide

图式9. 铜催化2-卤代芳基醛与2-羟基苯乙氰制备取代苯并[b]呋喃的可能机理

Scheme 9. Plausible mechanism of synthesis of substituted benzo[b]furans from 2-haloarylaldehydes and 2-hydroxyphenylacetocyanide catalyzed by copper

图式10. 镍催化2-(2-碘苯氧基)-1-芳酮分子环化合成苯并[b]呋喃衍生物的可能机理

Scheme 10. Plausible mechanism of intramolecular cyclization of 2-(2-iodophenoxy)-1-arylketone to benzo[b]furan derivatives catalyzed by nickel

图式11. 金催化2-(碘乙炔基)-芳基酯的环异构化反应制备取代苯并[b]呋喃衍生物的可能机理

Scheme 11. Plausible mechanism of cycloisomerization of 2-(iodoacetyl)-aryl esters to prepare substituted benzo[b]furan derivatives catalyzed by gold

图式12. 铑催化2-羟基苯炔化合物与N-新戊酰氧基酰胺化物环化反应合成取代苯并[b]呋喃衍生物的可能机理

Scheme 12. Plausible mechanism for the synthesis of substituted benzo[b]furan derivatives by the cyclization of 2-hydroxy- phenylalkyne compounds with N-pivaloyloxy amides catalyzed by rhodium

图式13. 铑催化水杨醛和重氮化合物的环化反应合成取代苯并[b]呋喃衍生物的可能机理

Scheme 13. Plausible mechanism of cyclization of salicylaldehyde and diazo compounds to synthesize substituted benzo[b]furan derivatives catalyzed by rhodium

图式14. 铱催化的苄醇氢转移反应合成取代苯并[b]呋喃衍生物的可能机理

Scheme 14. Plausible mechanism of hydrogen transfer reaction of benzyl alcohol to synthesize substituted benzo[b]furan derivatives catalyzed by iridium

图式15. 铟催化邻炔基苯酚的分子内环化反应制备取代苯并[b]呋喃的可能机理

Scheme 15. Plausible mechanism of intramolecular cyclization of o-alkynylphenol to prepare substituted benzo[b]furans catalyzed by indium

图式16. 钪催化芳香酮化合物与1,4-苯醌反应合成取代苯并[b]呋喃衍生物的可能机理

Scheme 16. Plausible mechanism of reaction of aromatic ketones with 1,4-benzoquinone to synthesize substituted benzo[b]furan derivatives catalyzed by scandium

图式17. 甲烷磺酸存在下O-芳基羟胺与酮反应制备取代苯并[b]呋喃衍生物的可能机理

Scheme 17. Plausible mechanism of O-arylhydroxylamine reacting with ketone to prepare substituted benzo[b]furan derivatives in the presence of methanesulfonic acid

图式18. 碱作用下邻羟基苯甲酸酯与1,1-二氯乙烯反应制备取代苯并[b]呋喃衍生物的可能机理

Scheme 18. Plausible mechanism of synthesis of substituted benzo[b]furan derivatives by the reaction of o-hydroxybenzoate with 1,1-dichloroethylene in the presence of alkali

图式19. 邻羟基苯乙酮与氯代酰胺制备2-酰胺苯并[b]呋喃类物质

Scheme 19. Benzo[b]furan-2-carboxamides from ortho-acetylphenols and 2-chloroacetamides

图式20. 二取代苯并呋喃的合成

Scheme 20. Synthesis of 2-substitute benzofurans

图式21. 氟化铯作用下三氟甲磺酸(2-三甲基硅基)苯酯与硫叶立德反应制备取代苯并[b]呋喃衍生物的可能机理

Scheme 21. Plausible mechanism of preparation of substituted benzo[b]furan derivatives by the reaction of trifluoromethanesulfonic acid (2-trimethylsilyl)phenyl ester with thioylide in the presence of cesium fluoride

图式22. K2CO3作用下烯醛与2-卤代酚反应制备取代苯并[b]呋喃衍生物的可能机理

Scheme 22. Plausible mechanism of synthesis of substituted benzo[b]furan derivatives by the reaction of enals with 2-halophenol in the presence of K2CO3

图式24. 碱作用下硝基环氧化物和水杨醛反应制备取代苯并[b]呋喃衍生物的可能机理

Scheme 24. Plausible mechanism of synthesis of substituted benzo[b]furan derivatives by the reaction of nitroepoxide and salicylaldehyde in the presence of alkali

图式24. 醋酸碘苯作用下邻羟基苯乙烯衍生物环化制备取代苯并[b]呋喃衍生物的可能机理

Scheme 24. Plausible mechanism of preparation of substituted benzo[b]furan derivatives by the cyclization of o-hydroxystyrene derivatives in the presence of iodobenzene acetate

图式25. 醋酸碘苯作用下邻羟基苯乙烯衍生物环化制备取代苯并[b]呋喃化合物的可能机理

Scheme 25. Plausible mechanism of preparation of substituted benzo[b]furans by the cyclization of o-hydroxystyrene derivatives in the presence of iodobenzene acetate

图式26. 1-(2-羟基苯基)-2-氯乙酮与格氏试剂反应制备苯并[b]呋喃衍生物的的可能机理

Scheme 26. Plausible mechanism of preparation of benzo[b]furan derivatives by the reaction of 1-(2-hydroxyphenyl)-2-chloroethanone with Grignard reagent

图式27. 钯催化苯并[b]呋喃与芳基咪唑硼酸盐反应制备苯并[b]呋喃衍生物的可能机理

Scheme 27. Plausible mechanism of reaction of benzo[b]furan with arylimidazole borate to prepare benzo[b]furan derivatives catalyzed by palladium

图式28. 钯催化有机铝试剂和2-卤代苯并[b]呋喃的偶联反应制备2-取代苯并[b]呋喃衍生物的可能机理

Scheme 28. Plausible mechanism of coupling reaction of organoaluminum reagent with 2-halobenzo[b]furan to prepare 2- substituted benzo[b]furan derivatives by palladium catalyzed

图式29. 钯催化苯并[b]呋喃与碘苯衍生物反应制备取代苯并[b]呋喃的可能机理

Scheme 29. Plausible mechanism of reaction of benzo[b]furan with iodobenzene derivatives to prepare 2-substituted benzo[b]- furan catalyzed by palladium

图式30. 铜催化苯并呋喃与邻苯甲酰羟胺进反应制备2-取代苯并[b]呋喃衍生物

Scheme 31. Synthesis of 2-substituted benzo[b]furan derivatives by copper catalyzed reaction of benzofuran with o-benzoyl hydroxylamine

图式31. 光催化3-碘色酮和苯并[b]呋喃反应合成2-取代苯并[b]呋喃衍生物的可能机理

Scheme 31. Plausible mechanism of synthesis of 2-substituted benzo[b]furan derivatives from 3-iodothrone and benzo[b]furan by photocatalytic

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