13372-76-4Relevant academic research and scientific papers
Cascade Process for Direct Transformation of Aldehydes (RCHO) to Nitriles (RCN) Using Inorganic Reagents NH2OH/Na2CO3/SO2F2 in DMSO
Fang, Wan-Yin,Qin, Hua-Li
, p. 5803 - 5812 (2019/05/14)
A simple, mild, and practical process for direct conversion of aldehydes to nitriles was developed feathering a wide substrate scope and great functional group tolerability (52 examples, over 90% yield in most cases) using inorganic reagents (NH2OH/Na2CO3/SO2F2) in DMSO. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable nitriles in a pot, atom, and step-economical manner without transition metals. This protocol will serve as a robust tool for the installation of cyano-moieties to complicated molecules.
7-Oxa-4-thia-1-aza-bicyclo[3.2.1]octane 4,4-Dioxides: Mechanochemical Synthesis by Tandem Michael Addition–1,3-Dipolar Cycloaddition of Aldoximes and Evaluation of Antibacterial Activities
Bhutia, Zigmee T.,Das, Avijit,Biswas, Malabika,Chatterjee, Amrita,Banerjee, Mainak
, p. 506 - 514 (2018/02/09)
A solvent-free, green, and efficient mechanochemical method for the synthesis of a series of bridged bicyclo aza-sulfone derivatives, namely 7-oxa-4-thia-1-aza-bicyclo[3.2.1]octane 4,4-dioxides through tandem Michael addition–1,3-dipolar cycloaddition of aldoximes was developed. Mechanochemical grinding/milling facilitates quick formation of aldoximes from corresponding aldehydes and hydroxylamine, which upon reaction with divinyl sulfone in a mixer mill affords 7-oxa-4-thia-1-aza-bicyclo[3.2.1]octane 4,4-dioxide derivatives in good overall yields. The newly synthesized bicyclo aza-sulfone derivatives 4 were screened for antibacterial activities. Mostly bicyclo aza-sulfones derived from electron-rich aromatic aldehydes inhibit the growth of Mycobacterium smegmatis (mc2155) and those from aliphatic aldehydes the growth of Escherichia coli (DH5α) in moderate to good effect. However, butyraldehyde-derived compound 4r was very effective against both M. smegmatis and E. coli. The key advantages of this mechanochemical method are catalyst- and solvent-free conditions, shorter reaction time, and formation of a new series of 7-oxa-4-thia-1-aza-bicyclo[3.2.1]octane 4,4-dioxide derivatives, which are good antibacterial agents against M. smegmatis and E. coli.
Nanocrystalline CeO2 as a Highly Active and Selective Catalyst for the Dehydration of Aldoximes to Nitriles and One-Pot Synthesis of Amides and Esters
Rapeyko, Anastasia,Climent, Maria J.,Corma, Avelino,Concepción, Patricia,Iborra, Sara
, p. 4564 - 4575 (2016/07/12)
The dehydration of aldoximes into nitriles has been performed in the presence of various metal oxides with different acid-base properties (Al2O3, TiO2, CeO2, MgO). The results showed that a nanocrystalline CeO2 was the most active catalyst. An in situ IR spectroscopy study supports a polar elimination mechanism in the dehydration of aldoxime on metal oxide catalysts, in which Lewis acid sites and basic sites are involved. The Lewis acid sites intervene in the adsorption of the oxime on the catalyst surface while surface base sites are responsible for the C1-H bond cleavage. Thus, the acid-base properties of nanocrystalline CeO2 are responsible for the high catalytic activity and selectivity. A variety of aldoximes including alkyl and cycloalkyl aldoximes have been dehydrated into the corresponding nitriles in good yields (80-97%) using nanosized ceria which moreover resulted in a stable and reusable catalyst. Additionally, it has been showed that a variety of pharmacologically important products such as picolinamide and picolinic acid alkyl ester derivatives can be obtained in good yields from 2-pyridinaldoxime in a one-pot process using the nanoceria as catalyst.
A versatile and green mechanochemical route for aldehyde-oxime conversions
Aakeroey, Christer B.,Sinha, Abhijeet S.,Epa, Kanishka N.,Spartz, Christine L.,Desper, John
supporting information, p. 11289 - 11291,3 (2012/12/12)
A robust, facile and solvent-free mechanochemical path for aldehyde-oxime transformations using hydroxylamine and NaOH is explored; the method is suitable for aromatic and aliphatic aldehydes decorated with a range of substituents. This journal is
A tungsten-tin mixed hydroxide as an efficient heterogeneous catalyst for dehydration of aldoximes to nitriles
Yamaguchi, Kazuya,Fujiwara, Hiroshi,Ogasawara, Yoshiyuki,Kotani, Miyuki,Mizuno, Noritaka
, p. 3922 - 3925 (2008/03/11)
(Chemical Equation Presented) Mix and match: A tungsten-tin mixed hydroxide (W-Sn hydroxide), prepared by the simple coprecipitation method, acts as a reusable heterogeneous catalyst for the dehydration of various aldoximes to the corresponding nitriles (see scheme, top). Furthermore, the W-Sn hydroxide catalyst could be applied to the direct one-pot synthesis of nitriles from hydroxylamine and the corresponding aldehydes (see scheme, bottom).
A one-pot synthesis of primary amides from aldoximes or aldehydes in water in the presence of a supported rhodium catalyst
Fujiwara, Hiroshi,Ogasawara, Yoshiyuki,Yamaguchi, Kazuya,Mizuno, Noritaka
, p. 5202 - 5205 (2008/03/13)
(Equation Presented) Dehydration/Rehydration in Water: Supported rhodium hydroxide (Rh(OH)x/ Al2O3) is an effective heterogeneous catalyst for the synthesis of primary amides from aldoximes and aldehydes in water in a reaction that is entirely free of hazardous and carcinogenic organic solvents (see scheme).
OXIDATION OF PRIMARY ALIPHATIC AMINES WITH SODIUM PERBORATE
Zajac, Walter W.,Darcy, Michael G.,Subong, Amador P.,Buzby, John H.
, p. 6495 - 6496 (2007/10/02)
A biphasic system of ethyl acetate and water containing sodium perborate, sodium bicarbonate and N,N,N',N'-tetraacetylethylenediamine oxidizes primary aliphatic amines to aliphatic C-nitroso compounds in good to excellent yields.
