By Desmond J. Brown
Drawing from over 2,500 papers, this quantity removes the necessity for time-consuming literature surveys for pyrimidines from 1970 via 1983. Chapters summarize the most important advances in pyrimidine chemistry, aspect advances in equipment of fundamental synthesis of pyrimidines, replace all points of hydropyrimidines, and deal with contemporary advances within the ionization and spectra of pyrimidines.Content:
Chapter I advent to the Pyrimidines (H 1) (pages 1–19):
Chapter II The critical man made technique (pages 20–52):
Chapter III different tools of fundamental Synthesis (H eighty two) (pages 53–85):
Chapter IV Pyrimidine and Its C?Alkyl and C?Aryl Derivatives (H 116) (pages 86–93):
Chapter V Nitro?, Nitroso?, and Arylazo?Pyrimidines (H 138) (pages 93–109):
Chapter VI Halogenopyrimidines (H 162) (pages 110–165):
Chapter VII Hydroxy? and Alkoxy?Pyrimidines (H 227) (pages 166–201):
Chapter VIII Sulphur?Containing Pyrimidines (H 272) (pages 202–229):
Chapter IX The Aminopyrimidines (H 306) (pages 230–268):
Chapter X The N?Alkylated Pyrimidines and the Pyrimidine?N?Oxides (H 356) (pages 269–295):
Chapter XI The Pyrimidine Carboxylic Acids and similar Derivatives (H 389) (pages 296–321):
Chapter XII The diminished Pyrimidines (H 430) (pages 322–367): R. F. Evans
Chapter XIII The Ionization and Spectra of Pyrimidines (H 464) (pages 368–398):
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Additional info for Chemistry of Heterocyclic Compounds: The Pyrimidines, Supplement 1, Volume 16
F): 2-phenacylpyrimidine and phenylmagnesium bromide gave 2-P-hydroxyPP-diphenylethylpyrimidine (64) ;3008 and borohydride reduction of 4-ethoxyoxalylmethylpyrimidine (65) gave mainly 4-py-dihydroxypropylpyrimidine. 3009 H. The Modification of Substituents ( H 24) (1) Amino Groups ( H 24) (Ch. IX) Although transamination was not unknown in the pyrimidine series, this process has been used widely only in recent years. 2153The process seems to be more effective with 4- than with 2-aminopyrimidines.
Ethanol; sodium ethoxide; reflux; 6 hr. ethanol ; sodium ethoxide; reflux; 6 hr. methanol ; sodium methoxide; reflux' methanol; sodium methoxide; reflux; 2 hr. ethanol; sodium ethoxide ; reflux; 2 hr. ; no solvent ethanol ; sodium ethoxide ; reflux; 4 hr. aq. ) C ethanol; sodium et hoxide ; reflux; 3 hr. 2307 21 16 2193 2874 2183 2198 2227 2226 (continued) 4-ethoxycarbonyl-22517 ethylthio-5-fluoro-6hydroxy-h (I 0%) 5-acetamido-4-hydroxy-62223 methyl-2-methylthio- (3573 4-hydroxy-2-mercapto-6methyl- (80%) 4-hydroxy-2-mercapto-5methoxy-6-methoxymethyl- (667,) 2,4-dihydroxy-5,6-tetramethyleneJ (367,) 4-hydroxy-2-mercapto-6methyl-5-phenylazo- 6-heptadecyl-4-hydroxy-2mercapto- (93%) 5-hexyl-4-hydroxy-22204, mercapt0-6-rnethyl-~(48 yo) 2225 2-fluoromethyl-4-hydroxy-6methyl- (ca.
Use of p-Aldehydo Esters ( H 38) Condensations of amidines with aldehydo esters were poorly represented until recently. , in the synthesis of uracils and thiouracils. Among more interesting recent examples (not included in Table I) are the direct formation of 3-methyl-2-thiouracil (13) from ethyl PP-diethoxypropionate and N-methylthiourea 2195 (the structure was checked by conversion into 3-methyluracil); a procedure for the synthesis of uracil from urea and diethyl malate (instead of malic acid); 'lg6 and the advantageous use of as a condensing agent in sodium hydride21g7in place of making (crude) ethyl formylbutyrate and its subsequent condensation with thiourea to yield 5-ethyl-4-hydroxy-2-mercaptopyrimidine.
Chemistry of Heterocyclic Compounds: The Pyrimidines, Supplement 1, Volume 16 by Desmond J. Brown