Palladium-catalyzed cyclization of enediynes to benzopyranones

被引：28

作者：

Chang, Wei-Ren ^{[1
]}

Lo, Yu-Hsiang ^{[1
]}

Lee, Chia-Ying ^{[1
]}

Wu, Ming-Jung ^{[1
]}

机构：

[1] Kaohsiung Med Univ, Fac Med & Appl Chem, Kaohsiung, Taiwan

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2008年 / 350卷 / 09期

关键词：

alkynes; cyclization; dibenzo[b; d]pyranones; enediynes; heterocycles; palladium;

D O I：

10.1002/adsc.200700516

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Treatment of methyl 2-[6-substituted-3(Z)-hexen-1,5-diynyl]benzoates (1) with five mol% of palladium chloride and three equivalents of cupric chloride in refluxing acetonitrile gave dibenzo[b,d]pyran-6-ones (2) in modest to good yields.

引用

页码：1248 / 1252

页数：5

共 25 条

[1] Synthesis of graphislactones A-D through a palladium-mediated biaryl coupling reaction of phenyl benzoate derivatives [J].

Abe, H ;

Nishioka, K ;

Takeda, S ;

Arai, M ;

Takeuchi, Y ;

Harayama, T .

TETRAHEDRON LETTERS, 2005, 46 (18) :3197-3200

[2] Reaction of (Z)-1-aryl-3-hexen-1,5-diynes with sodium azide:: Synthesis of 1-aryl-1H-benzotriazoles [J].

Chen, ZY ;

Wu, MJ .

ORGANIC LETTERS, 2005, 7 (03) :475-477

[3] Diels-Alder reactions of 3-substituted coumarins in water and under high-pressure condition.: An uncatalyzed route to tetrahydro-6H-benzo[c]chromen-6-ones [J].

Girotti, R ;

Marrocchi, A ;

Minuti, L ;

Piermatti, O ;

Pizzo, F ;

Vaccaro, L .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01) :70-74

[4]

Heck R.F., 1985, PALLADIUM REAGENTS O

[5] Synthesis of 6H-dibenzo[b,d]pyran-6-ones from aryl 3-bromopropenoates via a sequential one-pot procedure using the sonogashira coupling-benzannulation reaction [J].

Kawasaki, T ;

Yamamoto, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (15) :5138-5141

[6] Synthesis of benzofulvenes by palladium-catalyzed cyclization of 1,2-dialkynylbenzenes [J].

Lee, Chia-Ying ;

Wu, Ming-Jung .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (21) :3463-3467

[7] Synthesis of carbazoles via an intramolecular cyclization of 2-(6-substituted 3(Z)-hexen-1,5-diynyl)anilines and their related molecules [J].

Lee, CY ;

Lin, CF ;

Lee, JL ;

Chiu, CC ;

Lu, WD ;

Wu, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (06) :2106-2110

[8]

Li J. J., 2000, PALLADIUM HETEROCYCL

[9] General and selective synthesis of (Z)-3-haloacrylates via palladium-catalyzed carbonylation of terminal alkynes [J].

Li, JH ;

Tang, S ;

Xie, YX .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (02) :477-479

[10] Novel and selective palladium-catalyzed annulations of 2-alkynylphenols to form 2-substituted 3-halobenzo[b]furans [J].

Liang, Yun ;

Tang, Shi ;

Zhang, Xu-Dong ;

Mao, Li-Qiu ;

Xie, Ye-Xiang ;

Li, Jin-Heng .

ORGANIC LETTERS, 2006, 8 (14) :3017-3020

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