Advanced search
Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 19, 1989 - Issue 5-6
Submit an article Journal homepage
196
Views
37
CrossRef citations to date
0
Altmetric
Original Articles

Selective Reduction of the N-O Bond in Heteroaromatic N-Oxides by TiCl4/SnCl2

Roman Balicki Institute of Organic Chemistry, Polish Academy of Sciences Kasprzaka 44/52, PL, 01-224, Warsaw, Poland
,
Lukasz Kaczmarek Institute of Organic Chemistry, Polish Academy of Sciences Kasprzaka 44/52, PL, 01-224, Warsaw, Poland
&
Marek Malinowski Institute of Organic Chemistry, Polish Academy of Sciences Kasprzaka 44/52, PL, 01-224, Warsaw, Poland
Pages 897-900 | Received 01 Sep 1988, Published online: 24 Oct 2006

Citations (37)

Keep up to date with the latest research on this topic with citation updates for this article.

Subscribe to citation updates

Read on this site (6)

Byung Woo Yoo & Min Chol Park. (2008) Mild and Efficient Deoxygenation of Amine‐N‐oxides with MoCl5/NaI System. Synthetic Communications 38:10, pages 1646-1650.
Read now
Jung Hwa Han, Kyung Il Choi, Joong Hyup Kim, Cheol Min Yoon & Byung Woo Yoo. (2006) Facile Deoxygenation of Amine‐N‐oxides With CoCl2 · 6H2O–Indium System. Synthetic Communications 36:4, pages 415-419.
Read now
Jung Hwa Han, Kyung Il Choi, Joong Hyup Kim & Byung Woo Yoo. (2004) Facile and Efficient Deoxygenation of Amine‐N‐oxides with Gallium in Water. Synthetic Communications 34:17, pages 3197-3201.
Read now
Byung Woo Yoo, Kwang Hyun Choi, Kyung Il Choi & Joong Hyup Kim. (2003) Mild and Efficient Deoxygenation of Amine-N-oxides with Titanium Tetrachloride-Indium System. Synthetic Communications 33:24, pages 4185-4189.
Read now
Roman Balicki, Marcin Cybulski & Grzegorz Maciejewski. (2003) An Efficient Deoxygenation of Heteroaromatic N-Oxides Using Zinc Dust/Ammonium Formate Reagent System. Synthetic Communications 33:23, pages 4137-4141.
Read now
Arumugasamy Jeevanandam, Charles Cartwright & Yong-Chien Ling. (2000) Indium-Mediated Deoxygenation of Nitrones, N-Oxides and Deoxygenative Reductive Coupling of Nitrones to Vicinal Diamines. Synthetic Communications 30:17, pages 3153-3160.
Read now

Articles from other publishers (31)

Ho Kyeong Ryu, Yun Do Song & Jun Hee Lee. (2024) Deoxygenation of N-heterocyclic N -oxides using isopropanol as a recyclable reductant . Organic Chemistry Frontiers 11:8, pages 2249-2268.
Crossref
D. M. Bystrov & L. L. Fershtat. (2024) Reactivity of 2-aminopyridine N-oxides. Russian Chemical Bulletin 73:1, pages 33-52.
Crossref
Adebimpe D. Adesina. 2023. Exploring Chemistry with Pyridine Derivatives. Exploring Chemistry with Pyridine Derivatives.
Se Hyun Kim, Ju Hyeon An & Jun Hee Lee. (2021) Highly chemoselective deoxygenation of N-heterocyclic N -oxides under transition metal-free conditions . Organic & Biomolecular Chemistry 19:16, pages 3735-3742.
Crossref
Vishnu Ji Ram, Arun Sethi, Mahendra Nath & Ramendra Pratap. 2019. The Chemistry of Heterocycles. The Chemistry of Heterocycles 3 391 .
De-Ping Zhu, Bao-Hua Xu, Yi-Ran Du & Suo-Jiang Zhang. (2018) SiCl4-catalyzed/PR3-mediated β-C(sp3)−H functionalization of nitrones to α,β-unsaturated imines and aromatic heterocycles. Tetrahedron 74:18, pages 2230-2238.
Crossref
Y. B. R. D. Rajesh. (2017) An Improved Rapid and Mild Deoxygenation of Amine N ‐oxides . Journal of Heterocyclic Chemistry 55:2, pages 486-491.
Crossref
Jinu Jeong, Kosuke Suzuki, Mitsuhiro Hibino, Kazuya Yamaguchi & Noritaka Mizuno. (2016) Selective Deoxygenation of Pyridine N ‐Oxides through Photoredox Catalysis of a Dilacunary Silicotungstate . ChemistrySelect 1:15, pages 5042-5048.
Crossref
Aljoša Bolje & Janez Košmrlj. (2013) A Selective Approach to Pyridine Appended 1,2,3-Triazolium Salts. Organic Letters 15:19, pages 5084-5087.
Crossref
Byung Woo Yoo, Ha Il Jung, Se Heon Kim, Young Sun Ahn & Ji Yong Choi. (2013) Selective and Efficient Deoxygenation of Amine-N-Oxides with CeCl 3 ·7H 2 O/Zinc System . Bulletin of the Korean Chemical Society 34:2, pages 359-360.
Crossref
James A. BullJames J. Mousseau, Guillaume Pelletier & André B. Charette. (2012) Synthesis of Pyridine and Dihydropyridine Derivatives by Regio- and Stereoselective Addition to N -Activated Pyridines . Chemical Reviews 112:5, pages 2642-2713.
Crossref
Narendra B. Gowda, Gopal Krishna Rao & Ramesha A. Ramakrishna. (2010) A chemoselective deoxygenation of N-oxides by sodium borohydride–Raney nickel in water. Tetrahedron Letters 51:43, pages 5690-5693.
Crossref
. (2008) A Facile and Efficient Deoxygenation of Amine-N-oxides with WCl 6 /NaI System . Bulletin of the Korean Chemical Society 29:5, pages 909-910.
Crossref
Sunil Kumar Singh, M. Srinivasa Reddy, Mangesh Mangle & K. Ravi Ganesh. (2007) Cu(I)-mediated deoxygenation of N-oxides to amines. Tetrahedron 63:1, pages 126-130.
Crossref
Byung Woo Yoo, Jin Woo Choi & Cheol Min Yoon. (2006) A facile and efficient deoxygenation of amine-N-oxides with Mo(CO)6. Tetrahedron Letters 47:1, pages 125-126.
Crossref
. (2005) A Facile Deoxygenation of Amine-N-oxides with NiCl 2 .6H 2 O/Indium System . Bulletin of the Korean Chemical Society 26:12, pages 1921-1922.
Crossref
. (2004) Mild and Efficient Deoxygenation of Amine-N-Oxides with FeCl 3 ·6H 2 O-Indium System under Ultrasonication . Bulletin of the Korean Chemical Society 25:11, pages 1633-1634.
Crossref
Weon-Bae Ko, Je-Heon Nam & Sung-Ho Hwang. (2004) The oxidation of fullerene[C60] with various amine N-oxides under ultrasonic irradiation. Ultrasonics 42:1-9, pages 611-615.
Crossref
. (2002) Mild and Efficient Deoxygenation of Amine-N-Oxides with Bis(cyclopentadienyl)titanium(Ⅳ) Dichloride-Indium System. Bulletin of the Korean Chemical Society 23:6, pages 797-799.
Crossref
J.S Yadav, B.V Subba Reddy & M.Muralidhar Reddy. (2000) Indium-mediated deoxygenation of amine-N-oxides in aqueous media. Tetrahedron Letters 41:15, pages 2663-2665.
Crossref
T. Ruhland & H. Künzer. (1996) Structurally diverse 2,6-disubstituted quinoline derivatives by solid-phase synthesis. Tetrahedron Letters 37:16, pages 2757-2760.
Crossref
. 1996. Comprehensive Heterocyclic Chemistry II. Comprehensive Heterocyclic Chemistry II 685 794 .
Nicholas Dennis. 1996. Comprehensive Heterocyclic Chemistry II. Comprehensive Heterocyclic Chemistry II 91 134 .
D. Sicker & H. Wilde. (1992) Synthese substituierter 2-Aminochinolin-1-oxide durch reduktive Cyclisierung substituierter 3-(2-Nitrophenyl)acrylnitrile. Journal f�r Praktische Chemie/Chemiker-Zeitung 334:1, pages 76-80.
Crossref
. 1992. Compendium of Organic Synthetic Methods. Compendium of Organic Synthetic Methods 141 164 .
Marek Malinowski, Łukasz Kaczmarek & Franciszek Rozpłoch. (1991) Reductive properties of low-valent titanium reagents. Mechanistic studies. J. Chem. Soc., Perkin Trans. 2:6, pages 879-883.
Crossref
Thomas L. Gilchrist. 1991. Comprehensive Organic Synthesis. Comprehensive Organic Synthesis 381 402 .
Roman Balicki. (2006) TiCl 4 /NaI ‐ A Novel, Efficient Reagent for Mild Reduction of the N ‐ O Bond in Amine N ‐Oxides and Nitrones . Chemische Berichte 123:3, pages 647-648.
Crossref
R. BALICKI, L. KACZMAREK & M. MALINOWSKI. (2016) ChemInform Abstract: Selective Reduction of the N‐O Bond in Heteroaromatic N‐Oxides by TiCl4/SnCl2.. ChemInform 21:2.
Crossref
J G Keay & A R Sherman. 1990. Progress in Heterocyclic Chemistry - A critical review of the 1989 literature preceded by one chapter on a current heterocyclic topic. Progress in Heterocyclic Chemistry - A critical review of the 1989 literature preceded by one chapter on a current heterocyclic topic 166 184 .
Roman Balicki, Lukasz Kaczmarek & Marek Malinowski. (2006) Facile Reductive Cleavage of Oximes with a Low‐Valent Titanium Reagent. Liebigs Annalen der Chemie 1989:11, pages 1139-1140.
Crossref

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.