TITLE

One-pot conversion of �-aminocrotononitrile to secondary enaminonitriles including chiral ones ? Application to synthesis

AUTHOR(S)
Chatterjee, A.; Mishra, M.; Chowdhury, S. K. Dutta; Mahalanabis, Kumar K.
PUB. DATE
August 2005
SOURCE
Canadian Journal of Chemistry;Aug2005, Vol. 83 Issue 8, p1164
SOURCE TYPE
Academic Journal
DOC. TYPE
Article
ABSTRACT
A highly efficient one-pot conversion of �-aminocrotononitrile to secondary enaminonitriles including chiral ones is described. In contrast to �-aminocrotononitrile, some of these N-substituted �-enaminonitriles on reacting with acid chlorides show a unique preference for C-terminal selection allowing preparation of pyrazoles without separation of regioisomers. In addition, use of secondary enaminonitriles also provided access to pyrazoles that are not obtainable with primary enaminonitriles owing to an exclusive preference for N-terminal selection.
ACCESSION #
21377818

 

Related Articles

  • Mechanisms for the inversion of chirality: Global reaction route mapping of stereochemical pathways in a probable chiral extraterrestrial molecule, 2-aminopropionitrile. Kaur, Ramanpreet; Vikas // Journal of Chemical Physics;2015, Vol. 142 Issue 7, p1 

    2-Aminopropionitrile (APN), a probable candidate as a chiral astrophysical molecule, is a precursor to amino-acid alanine. Stereochemical pathways in 2-APN are explored using Global Reaction Route Mapping (GRRM) method employing high-level quantum-mechanical computations. Besides predicting the...

  • Synthesis of new pyrazole derivatives from benzylidenemalononitrile. Nosachev, S. B.; Shchurova, N. A.; Tyrkova, E. A; Tyrkov, A. G. // Russian Journal of Organic Chemistry;Mar2009, Vol. 45 Issue 3, p463 

    The article discusses the study on the synthesis of new pyrazole derivatives. The study views on the competing effects of functional groups in analog of 1-nitro-2-phenylethene, and examines its reactions with diazomethane and diazoethane. It states that the described reactions are open to a...

  • New synthesis of 3-aryl-5-amino-1H-pyrazoles. Nenaidenko, V.; Golubinskii, I.; Lenkova, O.; Shastin, A.; Balenkova, E. // Russian Journal of Organic Chemistry;Oct2004, Vol. 40 Issue 10, p1518 

    A new efficient procedure has been proposed for the synthesis of 3-aryl-5-amino-1H-pyrazoles by reaction of a-chloro-ß-arylacrylonitriles with hydrazine hydrate.

  • Synthesis of β -Ketonitriles from 3-Bromoisoxazoles. Kociolek, Martin G.; Straub, Nicholas G.; Marton, Elizabeth J. // Letters in Organic Chemistry;May2005, Vol. 2 Issue 3, p280 

    A series of substituted 3-bromoisoxazoles were ring opened with either molybdenum hexacarbonyl or iron (II)chloride tetrahydrate to give β -ketonitriles in good yields.

  • Reaction of 7-phenyl-7 H-pyrazolo-[3,4- d][1,2,3]triazin-4-ol with thionyl chloride. Khutova, B.; Klyuchko, S.; Gurenko, A.; Vasilenko, A.; Rusanov, E.; Brovarets, V. // Chemistry of Heterocyclic Compounds;Sep2013, Vol. 49 Issue 6, p922 

    The reaction of 7-phenyl-7 H-pyrazolo[3,4- d][1,2,3]triazin-4-ol with thionyl chloride has been studied in the presence and absence of dimethyl formamide. It was found that heating the compound with thionyl chloride in the absence of dimethyl formamide gave 5-amino-1-phenyl-1...

  • Unusual reaction of chloroacetyl chloride with 1,2-dichloroethene. Synthesis and properties of 2-chlorovinyl dichloromethyl ketone. Bozhenkov, G.; Savosik, V.; Rudyakova, E.; Khan�, Kha; Albanov, A.; Klyba, L.; Mirskova, A.; Levkovskaya, G. // Russian Journal of Organic Chemistry;Dec2008, Vol. 44 Issue 12, p1745 

    The reaction of chloroacetyl chloride with 1,2-dichloroethene in the presence of AlCl3 unexpectedly led to the formation of ( E)-1,1,4-trichlorobut-3-en-2-one whose structure was proved by 1H and 13C NMR, IR, and mass spectra and independent synthesis. A probable reaction scheme was proposed,...

  • A Facile One Pot Synthesis Of Pyrano[2,3-C]Pyrazole Derivatives Using P-Toluene Sulfonic Acid In Aqueous Media. HERAVI, Majid M.; JAVANMARDI, Najme; OSKOOIE, Hossein A.; BAGHERNEJAD, Bita // Gazi University Journal of Science;2011, Vol. 24 Issue 2, p227 

    A high yielding and fast method for the synthesis of 1,4-Dihydropyrano[2,3-c] pyrazole via one-pot, three component reaction of an aromatic aldehyde, malonitrile and 3-methyl-l-phenyl-2-pyrazolin-5-one using p-toluene sulfonic acid as a catalyst is described

  • Inner-sphere condensation of EtNCO and MeCN through coinsertion into the Re-Cl bond. Ovchinnikova, N.; Sinyakov, A.; Noskova, O.; Minaeva, N. // Inorganic Materials;Jul2012, Vol. 48 Issue 7, p745 

    Reactions of rhenium pentachloride with ethyl isocyanate in dichloroethane and acetonitrile are the first to demonstrate the feasibility of inserting organic isocyanates and nitriles into a rhenium-halogen bond. IR spectroscopy and elemental analysis data show that the addition of one to three...

  • A new one-pot synthesis of 1,2,4-oxadiazoles from aryl nitriles, hydroxylamine and crotonoyl chloride. ZAKERI, MASOUMEH; HERAVI, MAJID; ABOUZARI-LOTF, EBRAHIM // Journal of Chemical Sciences;Jul2013, Vol. 125 Issue 4, p731 

    The reaction of aryl nitriles with hydroxylamine using acetic acid as a catalyst followed by subsequent addition of crotonoyl chloride to the intermediate amidoxime represents a straightforward one-pot access to new 1,2,4-oxadiazole synthesis under mild conditions. The course of the reaction was...

Share

Read the Article

Courtesy of VIRGINIA BEACH PUBLIC LIBRARY AND SYSTEM

Sign out of this library

Other Topics