Synthesis of hexacyclic fused isocoumarin framework through selective domino multicyclizations under catalyst and solvent free conditions

被引：6

作者：

Babar, Tariq Mahmood ^{[1
]}

Naseer, Muhammad Moazzam ^{[1
]}

Rauf, Muhammad Khawar ^{[1
]}

Pervez, Humayun ^{[2
]}

Ebihara, Masahiro ^{[3
]}

Rama, Nasim Hasan ^{[1
]}

机构：

[1] Quaid I Azam Univ, Dept Chem, Islamabad 45320, Pakistan

[2] Bahauddin Zakariya Univ, Div Organ Chem, Inst Chem Sci, Multan 60800, Pakistan

[3] Gifu Univ, Fac Engn, Dept Chem, Gifu 5011193, Japan

来源：

CHINESE CHEMICAL LETTERS | 2014年 / 25卷 / 09期

关键词：

Hexacyclic; Fused isocoumarin; One pot; Catalyst and solvent free; ELLAGIC ACID; COUMARIN DERIVATIVES; CARCINOMA CELLS; RINGS; SKELETONS; ANTIOXIDANT; CYCLIZATION; ANALOGS; DESIGN; CONSTRUCTION;

D O I：

10.1016/j.cclet.2014.03.022

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel fused isocoumarin skeleton has been synthesized through selective domino multicyclizations by mixing homothallic acid and 2,3-diphenylacryloyl chloride at 200 degrees C under catalyst and solvent free reaction conditions. Six fused rings with two stereogenic centers were assembled in a convenient one-pot operation in good yield. The resulting hexacyclic fused isocoumarin skeleton and its stereochemistry was fully characterized and unambiguously confirmed by X-ray diffraction analysis. (C) 2014 Muhammad Moazzam Naseer and Nasim Hasan Rama. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

引用

页码：1282 / 1286

页数：5

共 54 条

[1] Access to the Akuammiline Family of Alkaloids: Total Synthesis of (+)-Scholarisine A
Adams, Gregory L.
Carroll, Patrick J.
Smith, Amos B., III
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (01) : 519 - 528
[2] Palladium-catalyzed and KOtBu-promoted Caryl-Oalcoholic coupling: an efficient one-pot synthesis of oxygen containing fused rings
Ahmed, Atiur
Dhara, Shubhendu
Ray, Jayanta K.
[J]. TETRAHEDRON LETTERS, 2013, 54 (13) : 1673 - 1676
[3] Simple coumarins and analogues in medicinal chemistry: Occurrence, synthesis and biological activity
Borges, F
Roleira, F
Milhazes, N
Santana, L
Uriarte, E
[J]. CURRENT MEDICINAL CHEMISTRY, 2005, 12 (08) : 887 - 916
[4] Cytotoxic effects, alkylating properties and molecular modelling of coumarin derivatives and their phosphonic analogues
Budzisz, E
Brzezinska, E
Krajewska, U
Rozalski, M
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2003, 38 (06) : 597 - 603
[5] Assembly of 3-Substituted Isocoumarins via a Cul-Catalyzed Domino Coupling/Addition/Deacylation Process
Cai, Shangjun
Wang, Fei
Xi, Chanjuan
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (05) : 2331 - 2336
[6] Synthesis of Functionalizable Boron-Containing π-Electron Materials that Incorporate Formally Aromatic Fused Borepin Rings
Caruso, Anthony, Jr.
Siegler, Maxime A.
Tovar, John D.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (25) : 4213 - 4217
[7] Anti-inflammatory and anti-coagulatory activities of caffeic acid and ellagic acid in cardiac tissue of diabetic mice
Chao, Pei-chun
Hsu, Cheng-chin
Yin, Mei-chin
[J]. NUTRITION & METABOLISM, 2009, 6
[8] Comparison of the tetrazolium salt assay for succinate dehydrogenase with the cytosensor microphysiometer in the assessment of compound toxicities
Cooke, D
O'Kennedy, R
[J]. ANALYTICAL BIOCHEMISTRY, 1999, 274 (02) : 188 - 194
[9] Urolithin as a Converging Scaffold Linking Ellagic acid and Coumarin Analogues: Design of Potent Protein Kinase CK2 Inhibitors
Cozza, Giorgio
Gianoncelli, Alessandra
Bonvini, Paolo
Zorzi, Elisa
Pasquale, Riccardo
Rosolen, Angelo
Pinna, Lorenzo A.
Meggio, Flavio
Zagotto, Giuseppe
Moro, Stefano
[J]. CHEMMEDCHEM, 2011, 6 (12) : 2273 - 2286
[10] Antioxidant activity of (+)-bergenin -: a phytoconstituent isolated from the bark of Sacoglottis uchi Huber (Humireaceae)
De Abreu, Heitor A.
Lago, Izandina Aparecida dos S.
Souza, Gilmar P.
Pilo-Veloso, Dorila
Duarte, Helio A.
Alcantara, Antonio Flavio de C.
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (15) : 2713 - 2718

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