Palladium-Catalyzed Synthesis of Isocoumarins and Phthalides via tert-Butyl Isocyanide Insertion

被引：103

作者：

Fei, Xiang-Dong ^{[1
]}

Ge, Zhi-Yuan ^{[1
]}

Tang, Ting ^{[1
]}

Zhu, Yong-Ming ^{[1
]}

Ji, Shun-Jun ^{[2
]}

机构：

[1] Soochow Univ, Coll Pharmaceut Sci, Suzhou 215123, Peoples R China

[2] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Suzhou 215123, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 22期

关键词：

HYDRANGEAE DULCIS FOLIUM; 3-SUBSTITUTED ISOCOUMARINS; INTRAMOLECULAR CYCLIZATION; ANTIFUNGAL ACTIVITY; INHIBITORY-ACTIVITY; DERIVATIVES; ACID; 3-YLIDENEPHTHALIDES; HETEROCYCLES; GENERATION;

D O I：

10.1021/jo302004u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and highly efficient strategy for the synthesis of isocoumarins and phthalides through a palladium(0)-catalyzed reaction incorporating tert-butyl isocyanide has been developed. This process, providing one of the simplest methods for the synthesis of this class of valuable lactones, involves two steps including cyclization reaction and simple acid hydrolysis. The methodology is tolerant of a wide range of substrates and applicable to library synthesis.

引用

页码：10321 / 10328

页数：8

共 41 条

[1] The structural diversity of phthalides from the Apiaceae [J].

Beck, John J. ;

Chou, Shen-Chieh .

JOURNAL OF NATURAL PRODUCTS, 2007, 70 (05) :891-900

[2] Anti-HIV activity of stilbene-related heterocyclic compounds [J].

Bedoya, Luis M. ;

del Olmo, Esther ;

Sancho, Rocio ;

Barboza, Blanca ;

Beltran, Manuela ;

Garcia-Cadenas, Ana E. ;

Sanchez-Palomino, Sonsoles ;

Lopez-Perez, Jose L. ;

Sanchez-Palomino, Sonsoles ;

Lopez-Perez, Jose ;

Munoz, Eduardo ;

Feliciano, Arturo San ;

Alcami, Jose .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (15) :4075-4079

[3] Regioselective synthesis of natural and unnatural (Z)-3-(1-alkylidene)phthalides and 3-substituted isocoumarins starting from methyl 2-hydroxybenzoates [J].

Bellina, F ;

Ciucci, D ;

Vergamini, P ;

Rossi, R .

TETRAHEDRON, 2000, 56 (16) :2533-2545

[4] Phthalides from Pittosporum illicioides var. illicioides with Inhibitory Activity on Superoxide Generation and Elastase Release by Neutrophils [J].

Chou, Tsung-Hsien ;

Chen, Ih-Sheng ;

Hwang, Tsong-Long ;

Wang, Tai-Chi ;

Lee, Tzong-Huei ;

Cheng, Lin-Yang ;

Chang, Ya-Chih ;

Cho, Jui-Ying ;

Chen, Jih-Jung .

JOURNAL OF NATURAL PRODUCTS, 2008, 71 (10) :1692-1695

[5] A new, expeditious entry to the benzophenanthrofuran framework by a Pd-catalyzed C- and O-arylation/PIFA-mediated oxidative coupling sequence [J].

Churruca, F ;

SanMartin, R ;

Tellitu, I ;

Domínguez, E .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (12) :2481-2490

[6] A NEW SYNTHESIS OF 3-YLIDENEPHTHALIDES VIA PALLADIUM-CATALYZED CYCLOCARBONYLATION OF 2-TRIFLYLOXYACETOPHENONES [J].

CIATTINI, PG ;

MASTROPIETRO, G ;

MORERA, E ;

ORTAR, G .

TETRAHEDRON LETTERS, 1993, 34 (23) :3763-3766

[7]

Feliciano A. S., 2003, BIOORG MED CHEM LETT, V13, P2769

[8] Synthesis of 3-Substituted Isocoumarins via a Cascade Intramolecular Ullmann-Type Coupling-Rearrangement Process [J].

Ge, Zhi-Yuan ;

Fei, Xiang-Dong ;

Tang, Ting ;

Zhu, Yong-Ming ;

Shen, Jing-Kang .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (13) :5736-5743

[9] Synthesis and antimicrobial activities of some isocoumarin and dihydroisocoumarin derivatives [J].

Hussain, M ;

Hussain, MT ;

Rama, NH ;

Hameed, S ;

Malik, A ;

Khan, KM .

NATURAL PRODUCT RESEARCH, 2003, 17 (03) :207-214

[10] First microwave-assisted synthesis of 3-substituted isocoutnarins [J].

Khana, KM ;

Ahmed, S ;

Khan, ZA ;

Rani, M ;

Perveen, S ;

Choudhary, ML ;

Atta-ur-Rahman .

LETTERS IN ORGANIC CHEMISTRY, 2005, 2 (06) :532-534

← 1 2 3 4 5 →