Recent Advances in the Synthesis of Pyrroles

Ferreira, Vı́tor F.; Souza, Maria Cecília B. V. de; Cunha, Anna C.; Pereira, Letícia Gonçalves; Ferreira, Maria Lurdes

doi:10.1080/00304940109356613

Cited by 209 publications

(32 citation statements)

References 132 publications

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“…Selected syntheses of more specialized derivatives, such as oxypyrroles, aminopyrroles, pyrrolines and pyrrolidines, are incorporated in the sections devoted to these systems. A review detailing many recent advances in pyrrole ring synthesis since 1995 is available [52], whereas a more specialized account provides a survey of routes to pyrroles bearing two aryl or heteroaryl groups on adjacent positions [53]. The Paal-Knorr pyrrole synthesis [54,55] deserves particular recognition as one the most valuable of all pyrrole ring forming reactions, as it relies on the condensation of 1,4-dicarbonyl compounds with primary amines or their equivalents, both of which are quite common and readily available materials.…”

Section: Pyrrole Ring Synthesismentioning

confidence: 99%

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Five‐Membered Heterocycles: Pyrrole and Related Systems

Bergman

Janosik

2011

Modern Heterocyclic Chemistry

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Section: Pyrrole Ring Synthesismentioning

confidence: 99%

“…Accounts concerning syntheses (e.g., by electropolymerization [50]), properties and applications of polypyrroles are also available [51,52].…”

Section: Chomentioning

confidence: 99%

Five‐Membered Heterocycles: Pyrrole and Related Systems

Bergman

Janosik

2011

Modern Heterocyclic Chemistry

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“…The pyrrole unit occurs in a diversity of synthetic pharmaceutical agents and is used as building blocks in many natural products syntheses [68]. Several substituted pyrroles show important biological activities such as selective inhibitors of the human cyclooxygenase-2 (COX-2) enzyme [69], high affinities for D2, D3, and D4 dopamine receptor subtypes [70] and also displays promising anticonvulsant activity [71].…”

Section: Pyrrole Synthesismentioning

confidence: 99%

Synthesis of Heterocyclic Compounds by Carbenoid Transfer Reactions

Ferreira

2007

COC

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“…In addition, the pyrrole framework represents some interest as a synthon, allowing access to various essential structures [66,68,[249][250][251][252][253][254]. Quite expectedly, a great interest caused by the importance and valuable properties of pyrroles is reflected in a number of excellent reviews on the synthesis of the pyrrole framework appearing recently in the literature [83,237,242,246,248,[255][256][257][258][259][260][261][262][263][264][265]. Apparently, a rational design of general and chemo-and regioselective transition metal-catalyzed methodologies for the pyrrole syntheses [79] still remains a challenging task for many research groups.…”

Section: Pyrrolesmentioning

confidence: 99%

Transition Metal‐Catalyzed Synthesis of Monocyclic Five‐Membered Aromatic Heterocycles

Dudnik

Gevorgyan

2010

Catalyzed Carbon‐Heteroatom Bond Formation

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Aromatic heterocycles, particularly furans and pyrroles, are structural motifs found in a vast number of biologically active natural and artificial compounds [1][2][3]. Other examples of practical applications of furans and pyrroles include dyes, polymers, and electronic materials [4]. Moreover, these heterocycles are employed as important intermediates in organic synthesis [5][6][7][8][9]. The successful application of furans and pyrroles in these and many other ways and their significance in applied and fundamental areas have placed them at the forefront of contemporary organic chemistry. A variety of methodologies and different protocols for their synthesis have been reported [1-3, 10-23] and become well established throughout decades. Among the variety of novel approaches for the synthesis of furans and pyrroles, transition metal-catalyzed transformations are arguably the most attractive methodologies . Several excellent reviews on the transition metal-catalyzed synthesis of monocyclic five-membered heterocycles have been published in the literature. Many of them were categorized by either the metal or the type of transformation. This chapter covers transition metal-catalyzed syntheses of furans and pyrroles. The main organization of this chapter is based on a heterocycle, wherein syntheses of a particular core are structured by the type of transformation and substrates engaged. Herein, we have tried to discuss equally the synthetic applicability of a method and mechanistic aspects and concepts implicated in the described transformations. A discussion of the mechanisms is given when needed to provide an idea about possible reaction pathways and the nature of the elementary processes involved in the catalytic transformation. It should be noted that the most essential and general catalytic reactions, as well as recent and conceptionally interesting transformations, are discussed in more detail in this chapter. Syntheses of furans and pyrroles via functionalization of the preexisting heterocyclic cores [37,[52][53][54][55][56][57][58][59][60] are not covered and, therefore, only reactions in which assembly of a heterocyclic ring occurs are described. In addition, the Pd-catalyzed synthesis of heterocycles is not covered herein, as this topic is covered in Chapter 6.

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Recent Advances in the Synthesis of Pyrroles

Cited by 209 publications

References 132 publications

Five‐Membered Heterocycles: Pyrrole and Related Systems

Five‐Membered Heterocycles: Pyrrole and Related Systems

Synthesis of Heterocyclic Compounds by Carbenoid Transfer Reactions

Transition Metal‐Catalyzed Synthesis of Monocyclic Five‐Membered Aromatic Heterocycles

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