Efficient One-Step Synthesis of 2-Arylfurans by Ceric Ammonium Nitrate (CAN)-Mediated Cycloaddition of 1,3-Dicarbonyl Compounds to Alkynes

Byung So Kim; Myung Whan Byun; Yong Rok Lee

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Efficient One-Step Synthesis of 2-Arylfurans by Ceric Ammonium Nitrate (CAN)-Mediated Cycloaddition of 1,3-Dicarbonyl Compounds to Alkynes

机译：硝酸铈铵（CAN）介导的1,3-二羰基化合物与炔烃的环加成反应，一步法合成2-芳基呋喃

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An efficient method for construction of 2-arylfiirans has been developed by ceric(IV) ammonium nitratemediated oxidative cycloaddition of cyclic and acyclic 1,3-dicarbonyl compounds to several alkynes. Reactions of 1,3-cyclohexanedione, 1,3-cyclopentanedione, and 2,4-pentanedione with several alkynes furnish 2-arylfurans in 26-75% yields. Extension of this technology to more complex 4-hydroxy-2-quinolone and 3-hydroxy-lH-phenalen-l-one with phenylacetylene also affords furoquinolinone and ftirophenalenone derivative in moderate yields. Reaction of 4-hydroxycoumarins with phenylacetylene give linear and angular furocoumarin derivatives as a mixture of regioisomer in good yields. The mechanistic pathway for the formation of 2-arylfurans has been also described.

机译：通过由硝酸铈（IV）铵介导的环状和非环状的1,3-二羰基化合物氧化成几个炔烃，已经开发出一种有效的构建2-芳基菲兰的方法。 1，3-环己二酮，1，3-环戊二酮和2，4-戊二酮与几种炔烃的反应以26-75％的产率提供了2-芳基呋喃。将该技术扩展为更复杂的4-羟基-2-喹诺酮和3-羟基-1H-苯并-1-酮与苯乙炔也能以中等收率得到呋喃喹啉酮和苯并菲烯酮衍生物。 4-羟基香豆素与苯乙炔的反应以良好的收率得到线性和有角的呋喃香豆素衍生物，为区域异构体的混合物。还描述了形成2-芳基呋喃的机制途径。

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《Bulletin of the Korean Chemical Society》 |1998年第10期|共页
作者
Byung So Kim; Myung Whan Byun; Yong Rok Lee;
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1. Efficient synthesis of dihydrofurans with sulfide groups by ceric(IV) ammonium nitrate-mediated oxidative cycloaddition of 1,3-dicarbonyl compounds to vinyl sulfides. Application to the synthesis of benzo[b]naphtho[2,3-d]furan-6,11-dione and first to [J] . Lee YR., Kang KY., Lee GJ., Synthesis: International Journal of Methods in Synthetic Organic Chemistry . 2003,第13期

机译：硝酸铈（IV）铵介导的1，3-二羰基化合物氧化成乙烯基硫化物可有效合成具有硫化基团的二氢呋喃。在苯并[b]萘并[2,3-d]呋喃-6,11-二酮的合成中的应用
2. Ceric ammonium nitrate (CBN)-mediated oxidative cycloaddition of 1,3-dicarbonyls to conjugated compounds. Efficient synthesis of dihydrofurans, dihydrofurocoumarins, dihydrofuroquinolinones, dihydrofurophenalenones, and furonaphthoquinone natural pro [J] . Lee YR., Kim DH., Kim BS. Tetrahedron . 2000,第45期

机译：硝酸铈铵（CBN）介导的1,3-二羰基与共轭化合物的氧化环加成反应。有效合成二氢呋喃，二氢呋喃香豆素，二氢呋喃喹啉酮，二氢呋喃富烯酮和呋喃萘醌天然脯氨酸
3. SYNTHESIS OF FUSED ACETALS BY CERIC AMMONIUM NITRATE MEDIATED CYCLOADDITION OF 1,3-DICARBONYL COMPOUNDS TO CYCLIC ENOL ETHERS [J] . Roy SC., Mandal PK. Tetrahedron . 1996,第38期

机译：硝酸铈铵介导的1，3-二羰基化合物在环烯醇中的缩合反应合成缩醛
4. Manganese-Catalyzed Construction of Tetrasubstituted Benzenes from 1,3-Dicarbonyl Compounds and Terminal Alkynes [C] . Mitsumi Nishi, Salprima Yudha S., Yoichiro Kumnobu Symposium on Organometallic Chemistry . 2008

机译：锰催化1,3-二羰基化合物和炔醇末端苯并的结构
5. I. Syntheses of E- and Z-volkendousin. II. Oxidative cyclization of unsaturated ketene dithioacetals with ceric ammonium nitrate to form bicyclic lactones. III. Synthesis of pyrinodemins A and B; assignment of the double bond position of pyrinodemin A. IV. Formal synthesis of guanacastepene A [D] . Shi, Bo 2003

机译：I.E-和Z-Volkendousin的合成。二。不饱和烯酮二硫缩醛与硝酸铈铵的氧化环化反应，形成双环内酯。三，嘧啶A和B的合成；嘧啶A的双键位置的分配。胍基丁烯A的形式合成
6. Efficient carbon-Ferrier rearrangement on glycals mediated by ceric ammonium nitrate: Application to the synthesis of 2-deoxy-2-amino-C-glycoside [O] . Alafia A Ansari, Y Suman Reddy, Yashwant D Vankar 2014

机译：硝酸铈铵介导的糖上碳-铁重排的高效重排：在合成2-脱氧-2-氨基-C-糖苷中的应用
7. Ceric Ammonium Nitrate(CAN)-Mediated Oxidative Cycloaddition of 1,3-Dicarbonyls to Viny Sulfides. Application to the Synthesis of Evodone and Avicequinone-B [O] . 2002

机译：酸铵硝酸铵（CAN）介导的氧化环加成1,3-二羰基对刚硫化物。应用于evodone和avicequinone-b的合成

Efficient One-Step Synthesis of 2-Arylfurans by Ceric Ammonium Nitrate (CAN)-Mediated Cycloaddition of 1,3-Dicarbonyl Compounds to Alkynes

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