RODD'S CHEMISTR Y OF CARBON COMPOUND S A modern comprehensive treatis e SECOND EDITIO N Edited b y S . COFFE Y M .Sc . (London), D.Sc . (Leyden), C .Chem ., F .R.I .C. formerly o f I .C.I . Dyestuffs Division, Blackley, Mancheste r VOLUME IV PART L HETEROCYCLIC COMPOUND S Fused-ring heterocyclic compounds containing three or more nitroge n atoms ; purines and related ring systems, nucleosides, nucleotides and nuclei c acids ; pteridines, alloxazines, flavins and related compounds . The bio - synthesis of plant alkaloids and nitrogenous microbial metabolites
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RODD'S CHEMISTRY OF CARBON COMPOUND S · Chapter 58. Nucleosides, Nucleotides and Nucleic Acids by D. S. E s 1 . Nucleosides 117 a. Structure of nucleosides 118 (r) The nature of
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RODD'S CHEMISTR Y
OF CARBON COMPOUND S
A modern comprehensive treatis e
SECOND EDITION
Edited by
S . COFFEYM.Sc. (London), D.Sc . (Leyden), C .Chem., F.R.I .C.
formerly ofI.C.I. Dyestuffs Division, Blackley, Mancheste r
VOLUME IV PART L
HETEROCYCLIC COMPOUND S
Fused-ring heterocyclic compounds containing three or more nitroge natoms ; purines and related ring systems, nucleosides, nucleotides and nuclei cacids ; pteridines, alloxazines, flavins and related compounds. The bio-
synthesis of plant alkaloids and nitrogenous microbial metabolites
Heterocyclic Compounds : Fused-ring heterocyclic compounds containing three or morenitrogen atoms ; purines and related ring systems ; nucleosides, nucleotides and nucleicacids ; pteridines, alloxazines, flavins and related compounds . The biosynthesis of plant
alkaloids and nitrogenous microbial metabolites
PREFACE VII
OFFICIAL PUBLICATIONS ; SCIENTIFIC JOURNALS AND PERIODICALS XIV
LIST OF ABBREVIATED NAMES OF CHEMICAL FIRMS MENTIONED IN PATENT REFERENCES .
X V
LIST OF COMMON ABBREVIATIONS AND SYMBOLS USED XVI
Chapter 57. Purines and Related Ring Systemsby G. SHA W
1 . Purities, imidazolo[4,5-d]pyrimidines 1a. General introduction 1b. Synthetic methods
4(i) Synthesis from pyrimidines, 5 - (ii) From imidazoles, 15 - (iii) Abiogenicsynthesis, 22 - (iv) Other syntheses, 25 -
30(i) Monohydroxypurines, 31 - (ii) Dihydroxypurines and their derivatives, 32 -(iii) Uric acid, 2,6,8-trihydroxypurine, 36 - (iv) N-Alkylhydroxypurines, 42 -(v) Alkoxypurines, 51 -
e. Halogenopurines
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(i) Methods of preparation, 52 - (ii) Properties and reactions, 55 - (iii) Individualhalogenopurines, 60 - (iv) Chlorohydroxypurines and their N-substitute dderivatives, 62 -
f. Mercaptopurines
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(i) Synthesis, 62 - (ii) Properties and reactions, 64 - (iii) Individual purinethiols ,65 -
g. Aminopurines
69(i) Methods of preparation, 70 - (ii) Properties. 72 - (iii) Individual amino-purines, 73 -
h. Aminohydroxypurines 8 3i. Nitropurines and related compounds 84j. Purine N-oxides
8 8(i) Purine 1-oxides, 88 - (ii) Purine 3-oxides, 90 - (iii) Purine 7- and 9-oxides ;7-hydroxypurines, 91 -
k. Spectra of purines
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(i) Ultraviolet, 96 - (ii) Infra-red, 98 - (iii) Proton magnetic resonance spectra ,98 - (iv) Mass spectra, 99 -
1 . Paper- and thin-layer-chromatography of purines 100