Copper nanoparticles catalyzed economical synthesis of 3-substituted isocoumarins from 2-chlorobenzoic acids/amides and 1,3-diketones

被引：10

作者：

Wang, Xiaowen ^{[1
]}

Wu, Chaolong ^{[1
]}

Sun, Youwen ^{[1
]}

Yao, Xiaoquan ^{[1
]}

机构：

[1] Nanjing Univ Aeronaut & Astronaut, Coll Mat Sci & Technol, Dept Appl Chem, Nanjing 210016, Peoples R China

来源：

TETRAHEDRON LETTERS | 2017年 / 58卷 / 32期

基金：

中国国家自然科学基金;

关键词：

3-Substituted isocoumarins; Copper nanoparticles catalyzed; 2-Chlorobenzoic acids; 2-Chlorobenzoic amides; 1,3-Diketones; O-IODOBENZOIC ACID; TERMINAL ALKYNES; ZINC-CHLORIDE; PHTHALIDES; DERIVATIVES; HETEROANNULATION; GENERATION;

D O I：

10.1016/j.tetlet.2017.07.001

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Copper nanoparticles were utilized as a highly efficient catalyst for a facile and economical synthesis of 3 substituted isocoumarins with 2-chlorobenzoic acids and 1,3-diketones as starting materials. The copper nanoparticles catalyst showed highly catalytic activity for the 2-chloro-substituted substrates to afford 3 substituted isocoumarins in good to excellent yields. Furthermore, good catalytic activity was also observed when 2-chlorobenzoic amides were utilized as substrates instead of the benzoic acids. (C) 2017 Published by Elsevier Ltd.

引用

页码：3164 / 3167

页数：4

共 50 条

[21] REACTIONS OF 3-ARYL-1-METHYL-1,3-DIKETONES WITH CYANOACETAMIDE CATALYZED BY LIPASE FROM CANDIDA-CYLINDRACEA .2.
MIJIN, DZ
MISICVUKOVIC, MM
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1995, 34 (04): : 348 - 350
[22] Efficient synthesis of 2-hydroxyalkyl alkanedithioates from 1,3-diketones, CS2, and epoxides
Yavari, Sima
Taherpour, Avat
Yavari, Issa
JOURNAL OF SULFUR CHEMISTRY, 2012, 33 (04) : 385 - 390
[23] Nitrile biotransformation for highly enantioselective synthesis of 3-substituted 2,2-dimethylcyclopropanecarboxylic acids and amides
Wang, MX
Feng, GQ
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02): : 621 - 624
[24] Nonpeptidic foldamers from amino acids: Synthesis and characterization of 1,3-substituted triazole oligomers
Angelo, NG
Arora, PS
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (49) : 17134 - 17135
[25] Nonpeptidic foldamers from amino acids: Synthesis and characterization of 1,3-substituted triazole oligomers
Angelo, Nicholas G.
Arora, Paramjit S.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
[26] 4-Dimethylaminopyridine-Catalyzed Benzannulation Reaction of Aromatic 1,3-Diketones with 3-Butyn-2-one
Zhou, Qingfa
Xin, Botao
Lu, Tao
Xue, Song
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2009, 29 (09) : 1462 - 1465
[27] InBr3-catalyzed annulations of cyclic 1,3-diketones with aryl propargyl alcohols: a novel synthesis of 2,4-diaryldihydropyrans
Yadav, J. S.
Reddy, B. V. Subba
Rao, K. V. Raghavendra
Narender, R.
TETRAHEDRON LETTERS, 2009, 50 (27) : 3963 - 3965
[28] Rhodium-Catalyzed Aerobic Decomposition of 1,3-Diaryl-2-diazo-1,3-diketones: Mechanistic Investigation and Application to the Synthesis of Benzils
Zhu, Jia-Liang
Tsai, Yi-Ting
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (01): : 813 - 828
[29] Copper-catalyzed One-Pot Synthesis of Isoindolinones from 2-Chlorobenzoic Acid, Aryl Alkynyl Carboxylic Acid, and Ammonium Acetate
Irudayanathan, Francis Mariaraj
Oh, Jonghoon
Lee, Sunwoo
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2015, 36 (07) : 1745 - 1746
[30] Synthesis of 3-arylazo-1H-pyridazin-4-ones from difluoroboron chelates of 1,3-diketones
Kravtsov, I. V.
Belyakov, P. A.
Baranin, S. V.
Dorokhov, V. A.
RUSSIAN CHEMICAL BULLETIN, 2007, 56 (08) : 1561 - 1565

← 1 2 3 4 5 →