Facile Synthesis of Disubstituted Isoxazoles from Homopropargylic Alcohol via C=N Bond Formation

被引：60

作者：

Gao, Pin ^{[1
]}

Li, Hong-Xia ^{[1
]}

Hao, Xin-Hua ^{[1
]}

Jin, Dong-Po ^{[1
]}

Chen, Dao-Qian ^{[1
]}

Yan, Xiao-Biao ^{[1
]}

Wu, Xin-Xing ^{[1
]}

Song, Xian-Rong ^{[1
]}

Liu, Xue-Yuan ^{[1
]}

Liang, Yong-Min ^{[1
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 24期

基金：

美国国家科学基金会;

关键词：

REGIOSPECIFIC SYNTHESIS; COPPER(I)-CATALYZED SYNTHESIS; NITRILE OXIDES; NITRATION; ACID; CYCLOADDITION; DECOMPOSITION; CONSTRUCTION; CONVERSION; ALKYNES;

D O I：

10.1021/ol503228x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel iron-catalyzed aerobic oxidative reaction to synthesize disubstituted isoxazoles from homopropargylic alcohol, t-BuONO, and H2O is developed. The method provides mild conditions to afford a variety of useful substituted heterocycles in an efficient and regioselective manner. The mechanism has been studied and proposed, which indicates that the transformation can be realized through construction of a C-N bond and C-O bond, CH oxidation, and then cyclization. Moreover, this method can be enlarged to gram scale.

引用

页码：6298 / 6301

页数：4

共 50 条

[31] tert-Butyl Nitrite Mediated Regiospecific Nitration of (E)-Azoarenes through Palladium-Catalyzed Directed C-H Activation [J].

Majhi, Biju ;

Kundu, Debasish ;

Ahammed, Sabir ;

Ranu, Brindaban C. .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (32) :9862-9866

[32] Synthesis of (E)-nitroolefins via decarboxylative nitration using t-butylnitrite (t-BuONO) and TEMPO [J].

Manna, Srimanta ;

Jana, Sandipan ;

Saboo, Tapish ;

Maji, Arun ;

Maiti, Debabrata .

CHEMICAL COMMUNICATIONS, 2013, 49 (46) :5286-5288

[33] Oxonium ion-mediated synthesis of 4-substituted spiro-isoxazolines [J].

McClendon, Eric ;

Omollo, Ann O. ;

Valente, Edward J. ;

Hamme, Ashton T., II .

TETRAHEDRON LETTERS, 2009, 50 (05) :533-535

[34] Direct Conversion of Arylamines to Pinacol Boronates: A Metal-Free Borylation Process [J].

Mo, Fanyang ;

Jiang, Yubo ;

Qiu, Di ;

Zhang, Yan ;

Wang, Jianbo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (10) :1846-1849

[35] REGIOSPECIFIC SYNTHESIS OF 3-SUBSTITUTED 5-ALKYLISOXAZOLES FROM OXIME DIANIONS AND N-METHOXY-N-METHYLALKYLAMIDES [J].

NITZ, TJ ;

VOLKOTS, DL ;

ALDOUS, DJ ;

OGLESBY, RC .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (19) :5828-5832

[36] SOLUBILITY AND DECOMPOSITION KINETICS OF NITROUS-ACID IN AQUEOUS-SOLUTION [J].

PARK, JY ;

LEE, YN .

JOURNAL OF PHYSICAL CHEMISTRY, 1988, 92 (22) :6294-6302

[37] Synthesis of Aryl Trimethylstannanes from Aryl Amines: A Sandmeyer-Type Stannylation Reaction [J].

Qiu, Di ;

Meng, He ;

Jin, Liang ;

Wang, Shuai ;

Tang, Shengbo ;

Wang, Xi ;

Mo, Fanyang ;

Zhang, Yan ;

Wang, Jianbo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (44) :11581-11584

[38] Synthesis of Pinacol Arylboronates from Aromatic Amines: A Metal-Free Transformation [J].

Qiu, Di ;

Jin, Liang ;

Zheng, Zhitong ;

Meng, He ;

Mo, Fanyang ;

Wang, Xi ;

Zhang, Yan ;

Wang, Jianbo .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (05) :1923-1933

[39] NOVEL CIS-HYDROXYLATION WITH NITROUS ACID [J].

RANGANAT.S ;

KAR, SK .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (11) :3962-&

[40] Accurate Rate Constants for Decomposition of Aqueous Nitrous Acid [J].

Rayson, Mark S. ;

Mackie, John C. ;

Kennedy, Eric M. ;

Dlugogorski, Bogdan Z. .

INORGANIC CHEMISTRY, 2012, 51 (04) :2178-2185

← 1 2 3 4 5 →