Efficient Synthesis of O-tert-Propargylic Oximes via Nicholas Reaction

Synthesis ◽  
2020 ◽  
Vol 52 (22) ◽  
pp. 3461-3465
Author(s):  
Itaru Nakamura ◽  
Keigo Shiga ◽  
Mao Suzuki ◽  
Masahiro Terada
Keyword(s):  
Ammonium Nitrate ◽  
Efficient Synthesis ◽  
Propargylic Alcohols ◽  
Cyclic Nitrones ◽  
Acidic Catalysts ◽  
Nicholas Reaction ◽  
High Yields ◽  
Dicobalt Hexacarbonyl ◽  
Cerium Iv Ammonium Nitrate

A synthetic protocol to access O-tert-propargylic oximes derived from tertiary propargylic alcohols was established via Nicholas reaction. Thus, BF3·OEt2-mediated reaction between the dicobalt hexacarbonyl complex of tert-propargylic alcohols and p-nitrobenzaldoxime followed by decomplexation with cerium(IV) ammonium nitrate afforded the corresponding O-tert-propargylic oximes in good to high yields. The obtained O-tert-propargylic oximes were effectively converted into heterocycles, such as four-membered cyclic nitrones, oxazepines, and isoxazolines, by using π-Lewis acidic catalysts.

Solid-state regioselective nitration of activated hydroxyaromatics and hydroxycoumarins with cerium (IV) ammonium nitrate

2005 ◽  
Vol 2005 (11) ◽  
pp. 733-735 ◽  
Author(s):  
Nemai C. Ganguly ◽  
Sanjoy Dutta ◽  
Mrityunjoy Datta ◽  
Prithwiraj De
Keyword(s):  
Solid State ◽  
Ammonium Nitrate ◽  
High Efficiency ◽  
Solvent Free ◽  
High Melting ◽  
Microwave Assisted ◽  
Solvent Free Conditions ◽  
High Yields ◽  
Regioselective Nitration ◽  
Cerium Iv Ammonium Nitrate

Predominant ortho-selective mononitration of low-melting and liquid phenols and hydroxycoumarins in moderate to high yields has been accomplished upon grinding with solid cerium (IV) ammonium nitrate (CAN). Microwave-assisted expeditious CAN-mediated nitration of relatively high melting phenols and hydroxycoumarins with high efficiency and selectively under solvent-free conditions has been also developed to address the problems of sluggishness and low yield for these reluctant substrates.

scholarly journals Cerium (IV) Ammonium Nitrate (CAN) Mediated Reactions IV. A Highly Efficient Synthesis of N,N’-Diarylsubstituted Formamidines in Water at Ambient Temperature

2011 ◽  
Vol 01 (03) ◽  
pp. 92-97 ◽  
Author(s):  
Kamal Usef Sadek ◽  
Abdulaziz Alnajjar ◽  
Ramadan Ahmed Mekheimer ◽  
Nasr Kamel Mohamed ◽  
Haney A. Mohamed
Keyword(s):  
Ambient Temperature ◽  
Ammonium Nitrate ◽  
Efficient Synthesis ◽  
Highly Efficient ◽  
Cerium Iv Ammonium Nitrate

Green and Facile Synthesis of Pyrimidine Derivatives Using Choline Chloride-urea Mixture as a Deep Eutectic Solvent or Cerium (IV) Ammonium Nitrate

2019 ◽  
Vol 23 (16) ◽  
pp. 1771-1777 ◽  
Author(s):  
Mohamed S. Behalo ◽  
Abdelmotaal Abdelmajeid ◽  
Aly A. Aly ◽  
Kaouser A. Hebash ◽  
Enas A. Mohamed
Keyword(s):  
Ammonium Nitrate ◽  
Choline Chloride ◽  
Deep Eutectic Solvent ◽  
Aromatic Aldehydes ◽  
Structural Formula ◽  
Facile Synthesis ◽  
Pyrimidine Derivatives ◽  
One Pot ◽  
High Yields ◽  
Cerium Iv Ammonium Nitrate

An efficient and facile synthesis of substituted pyrimidine derivatives through Biginelli type reaction was achieved in high yields via one-pot reaction of aromatic aldehydes, active methylene compounds and urea or thiourea in the presence of choline chloride- urea mixture as a deep eutectic solvent or cerium (IV) ammonium nitrate (CAN) as a catalyst at different conditions. The reaction was carried out using different ratio of CAN in different solvents to determine the optimum conditions. In addition, 2-mercapto-6-oxo- 4-(thiophen-2-yl)-1,6-dihydropyrimidine-5-carbonitrile was employed in the synthesis of pyrimidinylhydrazide and its corresponding hydrazone. The structural formula of all derivatives was confirmed and characterized by their elemental analyses and spectral data (IR, MS, 1H NMR, 13C NMR).

scholarly journals Efficient Synthesis of Isoquinoline Derivatives through Sequential Cyclization–Deoxygenation Reaction of 2-Alkynylbenzaldoximes

SynOpen ◽  
2022 ◽  
Vol 06 (01) ◽  
pp. 11-15
Author(s):  
Saeed Balalaie ◽  
Mojtaba Ayoubi ◽  
Ali Nikbakht ◽  
Kamran Amiri ◽  
Alireza Abbasi Kejani ◽  
...  
Keyword(s):  
Efficient Synthesis ◽  
Cyclization Reactions ◽  
Cyclic Nitrones ◽  
Silver Triflate ◽  
High Yields ◽  
Isoquinoline Derivatives

AbstractWe describe a novel, simple, robust, and efficient cyclization/deoxygenation approach for the synthesis of functionalized isoquinoline derivatives. Over the course of continued studies on o-alkynylbenzaldoxime cyclization reactions, the formation of cyclic nitrones through 6-endo-dig cyclization was achieved using silver triflate or bromine as an electrophile, and subsequently, the deoxygenation process was carried out in the presence of CS2 in good to high yields.

An Efficient Synthesis of 2-Substituted Quinazolin-4(3H)-ones by Using Recyclable Wang Resin Supported Sulfonic Acid Catalyst

2020 ◽  
Vol 17 ◽  
Author(s):  
Kalyani K. ◽  
Srinivasa Reddy Kallam
Keyword(s):  
Sulfonic Acid ◽  
Functional Group ◽  
Acid Catalyst ◽  
Sulphonic Acid ◽  
Isatoic Anhydride ◽  
Efficient Synthesis ◽  
Wang Resin ◽  
Polymer Supported ◽  
High Yields

Abstract:: An efficient synthesis of 2-substituted Quinazolin-4(3H)-ones has been developed from isatoic anhydride with various amidoximes by using recyclable polymer supported sulphonic acid catalyst. Excellent functional group compatibil-ity and high yields are the important features of this protocol.

scholarly journals Oxidative Modification of Native Protein Residues Using Cerium(IV) Ammonium Nitrate

2011 ◽  
Vol 133 (42) ◽  
pp. 16970-16976 ◽  
Author(s):  
Kristen L. Seim ◽  
Allie C. Obermeyer ◽  
Matthew B. Francis
Keyword(s):  
Ammonium Nitrate ◽  
Oxidative Modification ◽  
Native Protein ◽  
Protein Residues ◽  
Cerium Iv Ammonium Nitrate

Photochemistry of Cerium(IV) Ammonium Nitrate (CAN) in Acetonitrile

2021 ◽  
pp. 113440
Author(s):  
Evgeni M. Glebov ◽  
Vjacheslav P. Grivin ◽  
Victor F. Plyusnin ◽  
Roman G. Fedunov ◽  
Ivan P. Pozdnyakov ◽  
...  
Keyword(s):  
Ammonium Nitrate ◽  
Cerium Iv Ammonium Nitrate
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