By Richard A. Jones
Acylpyrroles (T. Toube).
Vinylpyrroles (B. Trofimov).
Aminopyrroles (G. Cirrincione, et al.).
3-Hydroxypyrroles (H. McNab & L. Monahan).
Chapter I Acylpyrroles (pages 1–129): Trevor P. Toube
Chapter II Vinylpyrroles (pages 131–298): Boris A. Trofimov
Chapter III Aminopyrroles (pages 299–523): Girolamo Cirrincione, Anna Maria Almerico, Enrico Aiello and Gaetano Dattolo
Chapter IV 3?Hydroxypyrroles (pages 525–616): Hamish Mcnab and Lilian C. Monahan
Read or Download Chemistry of Heterocyclic Compounds: Pyrroles, Part 2: The Synthesis, Reactivity, and Physical Properties of Substituted Pyrroles, Volume 48 PDF
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Additional resources for Chemistry of Heterocyclic Compounds: Pyrroles, Part 2: The Synthesis, Reactivity, and Physical Properties of Substituted Pyrroles, Volume 48
O 402 52 Acylpyrroles 203b - 404 MeO,C MMee o w . -NO2-4,51MeO),C,H, Pyrrolylhydrazones generally undergo the Wolff-Kishner reaction and may be used in the conversion of acylpyrroles into the corresponding alkyl derivati v e ~ . g. p. 152-154°C) in 86% yield. p. 278 410 41 1 412 R =CH,CI. CHCI,. CCI,. 4. 3. Reactions with Hydroxylamines Pyrrole aldehydes and ketones react in the usual manner with hydroxylamine to form o ~ i m e s . p. I 16"C);282 t,2-dibromo-l,I,2,2-tetrachloroethaneis 82%, significantly higher than that in carbon tetrachloride.
2 0 3Thiol and sulfoxide groups also stabilise adjacent carbanions, although not to the same extent as carbonyl groups. p. p. 206 In most of these reactions, only the E-isomers are produced, although in the case where R = CO,Et, the Z-isomer could also be isolated. '06 al"" Meo2 CO,Mr OHC + OC(CH2C0,Me), --+ Me 253 252 CHO OHC' Me Me 254 N R 255~ + MeSCH,COCH,SMe -----+ 255 a R-H b R=Me c R-Ph 256 H 257 d R=Bu 0 25511 + 0 MeSCH,COCH,SMe II II 0 0 2-% Me 259 - pR OHC 25% + ACH$, 0 M CH,0 260 R = Ph.
A more convenient synthesis involves the condensation of the formylpyrrole with Meldrum's acid to give 277a, that is, the protected analog of 228. p. p. p. 60--61"C)in 3 1 O h yield. p. p. 132 134°C) in 72% yield. In a different approach to the same ring system,221the anion 278 is allowed to react with phcnyl vinyl sulfone, followed by cyclization of the intermediate sulfone 284 to 285, which then reacts with a further two molecules of the sulfone to form 286, or with one molecule of sulfone to provide, after elimination of the equivalent of two molecules of phenylsulfinic acid, the tetracyclic system 287.