Chlorotropylium Promoted Conversions of Oximes to Amides and Nitriles

被引：17

作者：

Xu, Jiaxi ^{[1
]}

Gao, Yu ^{[1
]}

Li, Zhenjiang ^{[1
]}

Liu, Jingjing ^{[1
]}

Guo, Tianfo ^{[1
]}

Zhang, Lei ^{[1
]}

Wang, Haixin ^{[1
]}

Zhang, Zhihao ^{[1
]}

Guo, Kai ^{[1
]}

机构：

[1] Nanjing Tech Univ, Coll Biotechnol & Pharmaceut Engn, State Key Lab Mat Oriented Chem Engn, 30 Puzhu Rd South, Nanjing 211816, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 03期

基金：

中国国家自然科学基金;

关键词：

Amides; Organocatalysis; Rearrangement; Oximes; Tropylium; BECKMANN REARRANGEMENT; EPSILON-CAPROLACTAM; CYANURIC CHLORIDE; ALDOXIMES; CARBOCATION; KETOXIMES; CATION; MILD; DEHYDRATION; ACTIVATION;

D O I：

10.1002/ejoc.201901537

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chlorotropylium chloride as a catalyst for the transformations of oximes, ketones, and aldehydes to their corresponding amides and nitriles in excellent yields (up to 99 %) and in short reaction times (mostly 10-15 min). Oximes were electrophilically attacked on the hydroxyl oxygen by chlorotropylium. The produced tropylium oxime ethers were the key intermediates, of which the ketoxime ether led to amide through Beckmann rearrangement, and the aldoxime ether led to nitrile by nitrogen base DBU assisted formal dehydration. This chlorotropylium activation protocol offered general, mild, and efficient avenues bifurcately from oximes to both amides and nitriles by one organocatalyst.

引用

页码：311 / 315

页数：5

共 50 条

[21] Acceptor-Controlled Transfer Dehydration of Amides to Nitriles [J].

Okabe, Hiroyuki ;

Naraoka, Asuka ;

Isogawa, Takahiro ;

Oishi, Shunsuke ;

Naka, Hiroshi .

ORGANIC LETTERS, 2019, 21 (12) :4767-4770

[22] Highly convenient and efficient one-pot conversions of aldehydes into nitriles and ketones into amides using HY-zeolite [J].

Srinivas, KVNS ;

Reddy, EB ;

Das, B .

SYNLETT, 2002, (04) :625-627

[23] Conversion of aldoximes into nitriles and amides under mild conditions [J].

Tambara, Koujiro ;

Pantos, G. Dan .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (15) :2466-2472

[24] Fluorinated Vilsmeier Reagent: TFEDMA-mediated Synthesis of Aryl-cyanides and Aryl-amides via the Activation of Oximes† [J].

Yadav, Arvind K. ;

Reddy Narra, Srikanth ;

Zulfaqar Bacho, Muhamad ;

Sumii, Yuji ;

Shibata, Norio .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (06)

[25] Catalytic Conversion of Nitriles into Secondary- and Tertiary Amides [J].

Davulcu, Simge ;

Allen, C. Liana ;

Milne, Kirstie ;

Williams, Jonathan M. J. .

CHEMCATCHEM, 2013, 5 (02) :435-438

[26] Chitosan supported ionic liquid: a recyclable wet and dry catalyst for the direct conversion of aldehydes into nitriles and amides under mild conditions [J].

Khalafi-Nezhad, Ali ;

Mohammadi, Somayeh .

RSC ADVANCES, 2014, 4 (27) :13782-13787

[27] Visible-Light-Promoted Synthesis of Fluoroalkylated Oximes [J].

Lee, Da Seul ;

Hwang, Ho Seong ;

Cho, Eun Jin .

CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (17) :2405-2409

[28] Ultrasound-promoted synthesis of nitriles from aldoximes under ambient conditions [J].

Jiang, Nan ;

Ragauskas, Arthur J. .

TETRAHEDRON LETTERS, 2010, 51 (34) :4479-4481

[29] Organoselenium functionalized SBA-15 as a new catalyst for the cyanide-free conversion of oximes to nitriles [J].

Bigdelo, Maryam ;

Nemati, Firouzeh ;

Rangraz, Yalda .

BMC CHEMISTRY, 2022, 16 (01)

[30] Hydration of nitriles to amides in water by SiO2-supported Ag catalysts promoted by adsorbed oxygen atoms [J].

Shimizu, Ken-ichi ;

Imaiida, Naomichi ;

Sawabe, Kyoichi ;

Satsuma, Atsushi .

APPLIED CATALYSIS A-GENERAL, 2012, 421 :114-120

← 1 2 3 4 5 →