2305-75-1Relevant articles and documents
Design and synthesis of novel pyridopyrimidine derivatives with anchoring non-coplanar aromatic extensions of EGFR inhibitory activity
Eissa, Amal A.M.,Aljamal, Kholoud F.M.,Ibrahim, Hany S.,Abdelrasheed Allam, Heba
, (2021/09/06)
The present study describes the synthesis of three series of 4-substituted pyridopyrimidin derivatives 4a-h, 5a-d. 6a-d, starting from 2-amino-6-(4-methoxyphenyl)-4-(4-(substituted) phenyl)nicotinonitrile 2a-d via the reaction with N,N-dimethyl-N-' substi
Amidines. Part 31. pKa Values of N1,N1-Dialkyl-N2-phenylformamidines in Water-Ethanol Solutions
Oszczapowicz, Janusz,Jaroszewska-Manaj, Jolanta
, p. 1677 - 1680 (2007/10/02)
The pKa values of three series (30 compounds in all) of N1,N1-dialkyl-N2-phenylformamidines (XC6H4N=CHNRR) have been measured in water-ethanol mixtures.The obtained pKa values of the amidines have been correlated with Hammett-type substituent constants and the pKa values of the corresponding primary amines determined in the same solvent.The applicability of various ? values is discussed and it is shown that, in each case, for substituents on the phenyl ring at the amino nitrogen atom ?0 values should be used.It is found that the slopes of regression lines for correlations with Hammett-type constants depend on the substituents at the amino nitrogen atom, as well as on the solvent.
Amidines. Part 20. Rate of Reaction of N,N-Dialkylformamide Acetals with Substituted Anilines
Osek, Jerzy,Oszczapowicz, Janusz,Drzewinski, Witold
, p. 1961 - 1964 (2007/10/02)
Rate of reaction of seven N,N-dialkylformamide acetals R2N-CH(OR2)2 with a series of anilines substituted on the phenyl ring have been measured in benzene, methanol, chloroform, and tetrahydrofuran by use of a g.l.c. method.In each case studied reaction is irreversible and obeys a second-order kinetic equation.Reaction rates correlate with Hammett ? constants for substituents on the phenyl ring of the aniline molecule.On the basis of the kinetic data, the mechanism of reaction is discussed.
AMIDINES.PART XI. BASICITY OF N1,N1-DIMETHYLFORMAMIDINES
Oszczapowicz, Janusz,Raczynska, Ewa
, p. 419 - 428 (2007/10/02)
The pKa values of twenty four N1,N1-dimethyl-N2-phenyl- and N1,N1-dimethyl-N2-alkyl-formamidines in 95.6percent ethanol (azeotrope) at 25+/-0.2 degC have been measured by the potentiometric method.The pKa values of N2-phenyl derivatives obey Hammett equation and obtained ρ value is ca. 2/3 of that for symmetrically disubstituted N,N'-diphenylformamidines.It is shown that there is a good correlation, common for both N2-alkyl as well as for N2-aryl formamidines between pKa values of dimethylformamidines and pKa of corresponding primary amines.The slope of this correlation line is also ca. 2/3 of that for symmetricall y disubstituted N,N'-dialkyl- and N,N'-diarylformamidines.Experimental conditions securing reliable results of pKa determinations by potentiometric method in ethanol are discussed.
A Versatile New Synthesis of Quinolines and Related Fused Pyridines. Part 8. Conversion of Anilides into 3-Substituted Quinolines and into Quinoxalines
Meth-Cohn, Otto,Rhouati, Salah,Tarnowski, Brian,Robinson, Andrew
, p. 1537 - 1543 (2007/10/02)
Anilides (4) (ArNHCOCH2R) are readily converted into 2-chloro-3-R-quinolines (5) under Vilsmeier conditions and the 3-chloro-group may be removed with zinc and acetic acid yielding 3-substituted quinolines (7).When N-nitrosodialkylamines are used in place of dimethylformamide as the Vilsmeier agent, the anilides are converted into 2-chloroquinoxalines in low yields.Several by-products are formed and the mechanisms have been explored.Thus, the formation of ethyl N-arylcarbamate from the corresponding propionanilide is shown to involve an C->O alkyl migration related to a Wolff rearrangement, while N-arylformimidoyl dichloride (18), nitriles, and isocyanides are derived from C-C cleavage of the substituted side-chain.Variation of the acid chloride component of the Vilsmeier reagent or of the solvent was generally unproductive though use of phosphoryl bromide instead of the chloride caused conversion of anilides into bromoquinolines in low yields.
A Versatile New Synthesis of Quinolines and Related Fused Pyridines. Part 7. The Conversion of Acetamidothiophens into Thienopyridines
Meth-Cohn, Otto,Narine, Brahma,Tarnowski, Brian
, p. 1531 - 1536 (2007/10/02)
5-Substituted-2-acetamidothiophens are converted into 2-acetamidothiophen-3-carbaldehydes in good yield with equimolar amounts of dimethylformamide and phosphoryl chloride in hot dichloroethane.However, under similar conditions but with three mol of phosp
