The chemistry of triazine derivatives II. The acylation of 2,4,6-trimethyl-s-triazine to triazinyl ketones and their facile isomerization to acetamidopyrimidines

A series of triazinyl ketones has been prepared by acylating 2,4,6-trialkyl-s-triazines and these ketones have been isomerized to 4-acylamidopyrimidine derivatives. A possible mechanism for this isomerization is suggested.

[1]  C. Grundmann,et al.  Triazines. XXIV. The Conversion of Methyl-s-triazines into s-Triazine Aldoximes1 , 1964 .

[2]  M. R. Kamal,et al.  The Chemistry of Pyrazine and Its Derivatives. VIII. Diketones Derived from the Monoacylation of 2-Methyl-6-(acylmethyl)pyrazines and the Diacylation of 2,6-Dimethylpyrazine1 , 1964 .

[3]  C. W. Jefford,et al.  The Rearrangement of 5-Nitroso-6-aminopyrimidines to s-Triazines1a,b,2 , 1962 .

[4]  M. R. Kamal,et al.  The Chemistry of Pyrazine and Its Derivatives. VI. The Synthesis of Carbinols Containing the Pyrazine Nucleus1 , 1962 .

[5]  K. R. Huffman,et al.  Reaction of s-Triazine with Acidic α-Methylene Compounds1 , 1962 .

[6]  F. C. Schaefer,et al.  Synthesis of the s-Triazine System. III.1 Trimerization of Imidates , 1961 .

[7]  C. Grundmann,et al.  Triazines. XXIII. The Reaction of s-Triazine with Active Methylene Compounds1,2a , 1961 .

[8]  C. W. Jefford,et al.  A NOVEL REARRANGEMENT OF PYRIMIDINES TO s-TRIAZINES1 , 1961 .

[9]  N. T. McDevitt,et al.  Infrared Spectra of Some 1,3,5-Triazine Derivatives , 1960 .

[10]  S. Raynolds,et al.  The Synthesis of Nitrogen-containing Ketones. VIII. The Acylation of 3-Picoline, 4-Picoline and Certain of their Derivatives1-4 , 1960 .

[11]  R. Levine,et al.  Chemistry of Pyrazine and Its Derivatives. III. The Synthesis of Carbinols by the Participation of Methylpyrazine in Aldol-type Condensations1 , 1959 .

[12]  R. Levine,et al.  The Chemistry of Pyrazine and its Derivatives. II. The Acylation of Methylpyrazine1 , 1959 .

[13]  S. Mason 251. The tautomerism of N-heteroaromatic amines , 1959 .

[14]  W. Padgett,et al.  The Infrared Spectra of Some Derivatives of 1,3,5-Triazine , 1958 .

[15]  R. Levine,et al.  The Synthesis of Nitrogen-Containing Ketones. VII. A Study of the Acylation of 4-Picoline1,2 , 1957 .

[16]  W. Pfleiderer,et al.  Über Claisen‐Kondensationen mit Methylpyrimidinen , 1957 .

[17]  R. Branch Steric Influences on the Structure of Chelating Agents and on the Stability of Metal Chelates , 1957, Nature.

[18]  R. Branch Infra-red Spectra of Chelating Agents: 2-Phenacylpyridine Derivatives , 1956, Nature.

[19]  R. Levine,et al.  The Use of Organolithium Compounds to Effect the Alkylation of 2- and 4-Picoline1 , 1956 .

[20]  H. Sullivan,et al.  Claisen-like Condensation Reactions with 2,4,6-Trimethylpyrimidine , 1955 .

[21]  D. B. Lake,et al.  THE TRIMERIZATION OF GLYCOLONITRILE , 1954 .

[22]  P. Spoerri,et al.  Synthesis in the Pyridazine Series. II. The Preparation of Pyridazines from Substituted Maleic Anhydrides. Some Properties of 4-Methylpyridazine1 , 1954 .

[23]  A. Beckett,et al.  Some alkyl and acyl derivatives of 2-phenacylpyridine , 1954 .

[24]  G. Shaw,et al.  isoOxazolones. Part VI. The hydrogenation of 5-aminoisooxazoles. A new synthesis of pyrimidines , 1954 .

[25]  P. Russell The effects of substitution on the ultra-violet absorption spectra of phenylpyrimidines , 1954 .

[26]  C. Grundmann,et al.  Über Triazine, IV. Mitteil.: Phenyltriazin , 1953 .

[27]  A. W. Larchar,et al.  The Trimerization of Nitriles at High Pressures , 1952 .

[28]  R. Levine,et al.  THE SYNTHESIS OF NITROGEN-CONTAINING KETONES. II. KETONES DERIVED FROM 1- PICOLINE, QUINALDINE AND 2,6-LUTIDINE , 1952 .

[29]  C. Grundmann,et al.  Über Triazine, II. Mitteil.): Trimethyltriazin , 1951 .

[30]  R. Levine,et al.  THE SYNTHESIS OF HETEROCYCLIC NITROGEN-CONTAINING KETONES I. KETONES DERIVED FROM 2-PICOLINE. (Contribution No. 815) , 1951 .

[31]  W. A. Murphey,et al.  A Convenient Synthesis of the Monoalkylpyridines; a New Prototropic Reaction of 3-Picoline1,2 , 1951 .

[32]  John C. Roberts,et al.  74. An investigation of the reactions of phenyl-lithium with some methylpyrimidines , 1951 .

[33]  M. J. Weiss,et al.  The Acylation and Carbethoxylation of Quinaldine, Lepidine and α-Picoline Using Sodium Amide or Potassium Amide , 1949 .

[34]  C. Hauser,et al.  Alkaline cleavage of unsymmetrical beta-diketones; ring opening of acylcylohexanones to form epsilon-acyl caproic acids. , 1948, Journal of the American Chemical Society.

[35]  R. Seibert,et al.  THE ARYLALKYLATION OF PYRIDINES AND QUINOLINES METHYLATED IN THE 2- AND 4-POSITIONS1 , 1945 .

[36]  O. Poppenberg Zur Kenntniss der Pyridazine , 1901 .