Aromatic Vs diene reactivity of 2(1H)-pyridinone and its derivatives

Synthesis and Antimicrobial Activity of N‐Aryl‐4‐(cyano/alkoxycarbonyl)‐5‐(pyridin‐3‐yl)‐1H/3H‐1,2,3‐triazole Derivatives

“…In the present study, we have synthesized several new 1,2,3‐triazole derivatives containing pyridinyl‐ and cyano‐ or ester moieties directly attached to the triazole carbon atoms. Initially, chloroacetonitrile ( 1a ) was reacted with triphenylphosphine ( 2 ) in refluxing toluene for 8 h to obtain chlorotriphenylphosphoranylacetonitrile ( 3a ) in quantitative yield . Similarly, the reaction of 2 with either ethyl chloroacetate ( 1b ) or propan‐2‐yl chloroacetate ( 1c ) in dichloromethane at room temperature under stirring for 72 h gave ethyl or propan‐2‐yl chlorotriphenylphosphoranylacetic acid ester ( 3b or 3c ), respectively, in very good yield.…”

“…The synthesis of N ‐aryl‐5‐(pyridinyl)‐1 H /3 H ‐1,2,3‐triazole‐4‐carbonitriles is not reported so far. As part of our investigations on the conjugated alkynes , we have recently reported the synthesis of a new series of pyridine‐3‐yl‐substituted propynenitriles and acetylenic carboxylic acid esters by the intra‐molecular Wittig reaction of β‐oxo‐alkylidenetriphenylphosphoranes using microwave irradiation and conventional heating . The chloronicotinyl substituted acetylenic compounds have exhibited good antimicrobial activity.…”

“…Conjugated alkynenitriles and acetylenic carboxylic acid esters are good substrates for undergoing nucleophilic addition reactions. They are very good building blocks for preparing a variety of heterocyclic compounds . The present investigation is aimed at synthesizing a new series of N ‐aryl‐5‐(pyridin‐3‐yl)‐1 H /3 H ‐1,2,3‐triazole‐4‐carbonitriles and alkyl N ‐aryl‐5‐(pyridin‐3‐yl)‐1 H /3 H ‐1,2,3‐triazole‐4‐carboxylic acid esters by the 1,3‐dipolar cycloaddition reaction of 3‐(pyridin‐3‐yl)‐propynenitriles and the corresponding 3‐(hetero‐aryl)‐acetylenic carboxylic acid esters with aryl azides, for evaluating their antibacterial and antifungal activity.…”

AlBr3-Promoted stereoselective anti-hydroarylation of the acetylene bond in 3-arylpropynenitriles by electron-rich arenes: synthesis of 3,3-diarylpropenenitriles

“…The presence of conjugated acetylene and nitrile bonds in these compounds leads to an enhancement of reactivity of both functional groups. Thus, propynenitriles take part in electrophilic [1,2] and nucleophilic [3][4][5][6] addition reactions onto the acetylene bond leading to various substituted nitriles. Reactions onto both acetylene and nitrile groups are widely used for the construction of various heterocyclic systems [7][8][9][10][11][12][13][14][15].…”

Synthesis of 1-(1-Arylvinyl)pyridin-2(1H)-ones from Ketones and 2-Fluoropyridine

“…11 Rao et al have reported the nucleophilic addition to cyano-substituted aryl alkynes leading to 1-(1-arylvinyl)-2pyridones. 12 On the other hand, 2-halopydinium salts are easily converted into 2-pyridones. [13][14][15][16][17][18] Due to the toxicity of 2-chloropyridine, 19 the development of efficient synthetic routes to vinyl-2-fluoropyridinium salts are highly desirable in order to construct 1-(1-arylvinyl)-2-pyridones.…”