Catalytic Multicomponent Reactions for the Synthesis of <i>N</i>-Aryl Trisubstituted Pyrroles

Galliford, Chris V.; Scheidt, Karl A.

doi:10.1021/jo0624086

Cited by 149 publications

(39 citation statements)

References 34 publications

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“…Several new direct pyrrole syntheses based on multicomponent reactions (Section 4.4.10) have emerged recently, featuring for instance imines, diazoacetonitrile, and alkynes as the reactants in the presence of a rhodium(II) catalyst. The sequence of events leading to pyrroles presumably involves initial decomposition of the diazo compound, formation of an intermediate azomethine ylide upon reaction with the imine, and finally cycloaddition with the alkyne [726]. Similar sets of starting compounds, namely, imines, acid chlorides, and alkynes, may also be converted into pyrroles in the presence of either isocyanides [727] or phosphines [728].…”

Section: Addendummentioning

confidence: 99%

Five‐Membered Heterocycles: Pyrrole and Related Systems

Bergman

Janosik

2011

Modern Heterocyclic Chemistry

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Section: Addendummentioning

confidence: 99%

Five‐Membered Heterocycles: Pyrrole and Related Systems

Bergman

Janosik

2011

Modern Heterocyclic Chemistry

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“…A subsequent 5-endo-dig cyclization afforded a variety of 1,2,3,5-tetrasubstituted and even 1,2-fused pyrroles in moderate to good yields. 8 In their recent study, Scheidt and coworkers devised the Rh(II)-catalyzed methodology employing imines, activated alkynes and diazoacetonitrile (DAN) in a convergent three-component 2 þ 2 þ 1 assembly reaction leading to pyrrolo-3,4-dicarboxylates 359 in moderate to high yields (Scheme 8.124) [317]. The authors proposed that DAN reacts with the Rh(II) catalyst to generate the corresponding metallocarbenoid 360.…”

Section: %mentioning

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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“…Additionally, a study showed that a Lewis acid can activate to cyclopropanes which react with aliphatic, aromatic, and á,â-unsaturated nitriles via dipolar cycloaddition [3 + 2], following by dehydration, and a tautomerization sequence for preparation of pyrroles 6 . Another report indicated that the Dirhodium(II) reagent can used in the threecomponent system (imine, diazoacetonitrile, and an activated alkynyl) as catalyst to form substituted 1,2-diarylpyrroles 7 .In addition, a study showed that Au(I) reagent Catalyzed the reaction of aryl-substituted with N-tosyl alkynyl aziridines to give 2,5-substituted pyrroles 8 . Another study showed a rearrangement reaction of a propargylic-aziridine, catalyzed by PPh 3 AuCl/AgOTf, forming some pyrrole derivatives 9 .…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Two Steroid-Pyrrolo-Triazecin Derivatives Using Estrone and Pregnenolone as Chemical Tools

et al. 2017

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Several steroid-pyrrole derivatives have been prepared using different protocols; nevertheless, have some drawbacks such as the use of some reagents that have limited stability and require special conditions. The aim of study involved the synthesis of two steroid-pyrrolo-triazecin derivatives using a series of reactions that involve; cycloaddition [2 + 2], displacement of nitro group, formation of shift base, amidation/cyclization using boric acid (Method A) or carbodiimide derivative (Method B). The results showed that there is a higher yielding with the method A in comparison with the method B. In addition, chemical structure of compounds was confirmed by NMR spectroscopic data.

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Catalytic Multicomponent Reactions for the Synthesis of N-Aryl Trisubstituted Pyrroles

Cited by 149 publications

References 34 publications

Five‐Membered Heterocycles: Pyrrole and Related Systems

Five‐Membered Heterocycles: Pyrrole and Related Systems

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

Design and Synthesis of Two Steroid-Pyrrolo-Triazecin Derivatives Using Estrone and Pregnenolone as Chemical Tools

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