An Efficient Domino Approach for the Synthesis of Multisubstituted Pyrroles <i>via</i> Gold/Silver‐Catalyzed Amination/Cycloisomerization of (<i>Z</i>)‐2‐En‐4‐yn‐1‐ols

Lu, Yan; Fu, Xiang; Chen, Haoyi; Du, Xiangwei; Jia, Xueshun; Liu, Yuanhong

doi:10.1002/adsc.200800490

Cited by 106 publications

(34 citation statements)

References 84 publications

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“…The reaction occurs via amination of ( Z )-enynols 3-225 , followed by a cycloisomerization of the in situ generated ( Z )-(2-en-4-ynyl)amines 3-227 into pyrroles 3-226 (Scheme 236) 389 Alkyl- or aryl amines 3-229 undergo the reaction with more active acetoxy-( Z )-enynols 3-228 providing the corresponding N -arylsubstituted pyrroles 3-230 in good yields (Scheme 236). 390 …”

Section: Synthesis Of Pyrrolesmentioning

confidence: 99%

Transition Metal-Mediated Synthesis of Monocyclic Aromatic Heterocycles

et al. 2013

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Section: Synthesis Of Pyrrolesmentioning

confidence: 99%

Transition Metal-Mediated Synthesis of Monocyclic Aromatic Heterocycles

et al. 2013

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“…Recently, Liu disclosed a more general 4 þ 1 approach toward the synthesis of pyrroles, which combined an initial Au-catalyzed amination of (Z)-enynols 276 followed by cycloisomerization of in situ generated (Z)-(2-en-4-ynyl)amines 278 into pyrroles 279 in a cascade fashion (Scheme 8.100) [295]. This methodology provides a highly efficient and regioselective entry into fused, as well as acyclic tri-, tetra-and penta-substituted, pyrroles 279.…”

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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“…Classical methods available for pyrrole synthesis are Knorr, Pall-Knorr and Hantzsch approach. New methodologies for pyrrole synthesis include intramolecular cyclization, [5][6][7] transition-metal catalyzation, [8][9][10][11] and multi-component reactions. [12][13][14][15] All these methods are suffering from drawbacks of tedious workups, use of toxic or expensive transition metals, and unavailability of the starting materials.…”

Section: Introductionmentioning

confidence: 99%

“…entries[1][2][3][4][5][6][7][8][9]. Under this reaction conditions methoxy groups are stable (Table 2, entries…”

mentioning

confidence: 98%

Efficient, Three-Component Synthesis of Pyrrole Derivatives Catalyzed by Iodobenzene and Oxone

Jagadhane

Jadhav

Herlekar

et al. 2015

Synthetic Communications

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An Efficient Domino Approach for the Synthesis of Multisubstituted Pyrroles via Gold/Silver‐Catalyzed Amination/Cycloisomerization of (Z)‐2‐En‐4‐yn‐1‐ols

Cited by 106 publications

References 84 publications

Transition Metal-Mediated Synthesis of Monocyclic Aromatic Heterocycles

Transition Metal-Mediated Synthesis of Monocyclic Aromatic Heterocycles

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

Efficient, Three-Component Synthesis of Pyrrole Derivatives Catalyzed by Iodobenzene and Oxone

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