Chemistry of Heterocyclic Compounds: Pyrroles, Part 2: The by Richard A. Jones

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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

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Additional info for Chemistry of Heterocyclic Compounds: Pyrroles, Part 2: The Synthesis, Reactivity, and Physical Properties of Substituted Pyrroles, Volume 48

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Piperidine catalyzes the condensation with the pyridinium salt 148 to give the pyridinium analog 149 of a ~ t y r y l p y r r o l e . 3. Reactions of Acyl Groups with Carbon Nucleophiles 21 2-Formyl-1 -methylpyrrole (77b)reacts. p. ’ ’’) t 48 149 OSiMe, Me,SibOSiMe, 77b + 7 \ IS0 OSiMe, Me I C! p. ’60 I55 IS4 Tandem one-pot reductive alk ylations of pyrrolyl aldehydes and ketones have been reported. 'O' With N-protected acylpyrroles, however, the reaction is somewhat less problematical. '64 The authors claim this reaction to be general, leading to a range of precursors to substituted indoles via cleavage of the cyclic acetal, followed by cyclization onto the 3-position of the pyrrole ring.

H 369 372 370 37 1 a Ar=phenyl b Ar = 2-pyrrolyl The corresponding reactions with diamines are not straightforward. 4. ”’ With 1,3-diaminobenzene. 2-formylpyrrole (77a)again gives a bis-adduct 377,25’but it is reported that with 1,2-diaminobenzene either the bis-adduct 378 or the benzimidazole 379 may be formed. 2s3 377 HO 378 77a 379 Me The behavior of the 3,4-diformylpyrrole 381 with amines is anomalous. With aliphatic amines, efficient substitution for one of the chlorine atoms is the primary reaction; pyrrolidine and cyclohexylamine give 382 (65%) and 383 48 Acylpyrroles (56%), respectively.

117-1 IS'C),r e ~ p e c t i v e l y . ' ~ ~ 231 a R=Me b R=H 238 R=Me b R-Ph 8 P 239 R=Me b R=Ph Acylpyrroles 240 11 b 24 I n=('oIEt K-CN a R=Me b R-Ph With cyclic dicarbonyl compounds, the Knoevenagel reaction proceeds with equal efficiency. p. p. 3. Reactions of Acyl Groups with Carbon Nucleophiles The 3,4-diformylpyrrole 252 reacts with the 3-ketoglutaric ester 253 to yield the cyclic ketone 2 S . 2 0 3Thiol and sulfoxide groups also stabilise adjacent carbanions, although not to the same extent as carbonyl groups.

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