27036-90-4

Usage

Uses

Used in Pharmaceutical Industry:
2-METHYL-6-OXO-1,4,5,6-TETRAHYDRO-3-PYRIDINECARBONITRILE is used as a key intermediate in the synthesis of various drugs, leveraging its unique molecular structure and functional groups to create new therapeutic agents.
Used in Organic Chemistry:
In the field of organic chemistry, 2-METHYL-6-OXO-1,4,5,6-TETRAHYDRO-3-PYRIDINECARBONITRILE serves as a valuable building block for the development of innovative synthetic methodologies, enabling the creation of novel compounds with diverse applications.
Used in Drug Discovery and Development:
Due to its potential bioactive properties, 2-METHYL-6-OXO-1,4,5,6-TETRAHYDRO-3-PYRIDINECARBONITRILE may be explored for its potential in drug discovery and development, offering new avenues for the creation of effective pharmaceuticals.

InChI:InChI=1/C7H8N2O/c1-5-6(4-8)2-3-7(10)9-5/h2-3H2,1H3,(H,9,10)

Upstream product

• 763-33-7 (E)-3-aminocrotononitrile 
• 814-68-6 acryloyl chloride 
• 870-64-4 2-aminocrotononitrile 

Relevant academic research and scientific papers

2-Aza-1,3-dienes with electron-releasing substituents at the 1,3 positions. Reagents for the construction of pyridine and pyrimidine derivatives

New 2-aza-1,3-dienes bearing 1 and 3-donor substituents are prepared from N-thioacylacetamidines through deprotonation of N-ylidene acetamidinium iodides. The 2-aza-3-(dimethylamino)-1-(methylthio)-1-phenylbutadiene (3) is trapped in situ by the residual precursor salt acting as a heterodienophile to give the pyrimidine 5. Substituted 2-aza-1-(dimethylamino)-3-(methylthio) analogues react readily with a variety of electron-deficient dienophiles to yield pyridine or pyrimidine derivatives. The stereochemistry of the hetero Diels-Alder reaction in the cases of dimethyl fumarate and acrylonitrile has been assigned by X-ray diffraction analyses of the resulting tetrahydropyridines and corresponds to an exo selectivity. The number and nature of cycloadducts in the cases of dimethyl acetylenedicarboxylate and phenyl isothiocyanate depend on C-4 substitution. The results obtained from the C-4 unsubstituted azabutadiene 8 are explained by an allylic rearrangement involving the 1,3-migration of dimethylamino group in the primary [4+2] adduct.

Heterocycle Formation through Aza-Annulation: Stereochemically Controlled Syntheses of (+/-)-5-Epitashiromine and (+/-)-Tashiromine

N-alkenylamines, stabilized through conjugation with an electron-withdrawing group, undergo aza-annulation with acryloyl chloride to provide a convergent route for the construction of six-membered nitrogen heterocycles.In addition to enhancing the C-alkylation process of annulation relative to the competing N-acylation process, the electron withdrawing substituent controlled the regioselectivity of alkene formation in both the intermediate enamine and in the unsaturated lactam product.A variety of functional groups, which include -COMe, -COPh, -CO2R, -CONHPh, -CN, -P(O)(OEt)2, and -SO2Ph, were used to determine the effect of the electron-withdrawing substituents upon both the annulation reaction with acryloyl chloride and the subsequent hydrogenation process.When the enamide annulation product was stabilized through conjugation with ester or amide substituents, catalytic hydrogenation of the aza-annulation product resulted in the formation of vicinal stereocenters with high cis selectivity.The utility of this methodology was demonstrated by application of the condensation/aza-annulation/hydrogenation sequence as the key for construction and stereochemical control of the indolizidine ring system of (+/-)-tashiromine.

'Conformationally restricted β-amino acid isosteres prepared through regioselectively controlled aza-annulation'

A variety of electron withdrawing substituents were used to enhance the aza-annulation of enamines with acryloyl chloride, to direct the regioselectivity of alkene formation, and to facilitate hydrogenation of the unsaturated annulation product. The resul