Synthesis of Pyrroles and Their Derivatives from Isocyanides

Ono, Noboru; Okujima, Tetsuo

doi:10.1002/9783527652532.ch11

Cited by 10 publications

(4 citation statements)

References 176 publications

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“…Thus, nonfluorinated nitrostyrenes have found broad applications in the synthesis of different heterocycles . For example, the Barton–Zard reaction is a very useful method for the synthesis of pyrroles . It was demonstrated that a fairly rare type of fluoro-substituted pyrrole, 3-fluorinated pyrrole derivative 13 , can be constructed very efficiently using the reaction of 1a with ethyl isocyanoacetate in the presence of DBU as a base.…”

Section: Resultsmentioning

confidence: 99%

Radical Nitration-Debromination of α-Bromo-α-fluoroalkenes as a Stereoselective Route to Aromatic α-Fluoronitroalkenes—Functionalized Fluorinated Building Blocks for Organic Synthesis

et al. 2017

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A new highly efficient method for the synthesis of 2-fluoro-2-nitrostyrenes was described. Radical nitration of readily available 2-bromo-2-fluorostyrenes with Fe(NO)·9HO resulted in the formation of the corresponding α-fluoro-nitroalkenes in isolated yields up to 92%. The reaction proceeded as a nitration-debromination sequence to highly stereoselectively give α-fluoro-nitroalkenes as Z-isomers only. The broad scope of this method was demonstrated. Prepared monofluorinated alkenes were shown to be versatile building blocks for the synthesis of various fluorinated products.

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Section: Resultsmentioning

confidence: 99%

Radical Nitration-Debromination of α-Bromo-α-fluoroalkenes as a Stereoselective Route to Aromatic α-Fluoronitroalkenes—Functionalized Fluorinated Building Blocks for Organic Synthesis

et al. 2017

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“…Since pyrrole and its multi-substituted derivatives play an important role in organic synthesis as well as in biology, syntheses of five-membered heterocyclic pyrrole compounds have always been valued by researchers. Over the last decades, there are many methods for synthesizing pyrrole compounds in laboratory routes [ 14 ], and the classical methods include Knorr pyrrole synthesis [ 15 ], Paal-Knorr pyrrole synthesis [ 16 ], Hantzsch pyrrole synthesis [ 17 ], Barton-Zard reaction [ 18 ], Van Leusen pyrrole synthesis [ 19 ], and Piloty–Robinson pyrrole synthesis [ 20 ]. These synthesis methods are summarized in Scheme 1 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Multi-Substituted Pyrrole Derivatives Through [3+2] Cycloaddition with Tosylmethyl Isocyanides (TosMICs) and Electron-Deficient Compounds

Zhang

2018

Molecules

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Pyrrole and its polysubstituted derivatives are important five-membered heterocyclic compounds, which exist alone or as a core framework in many pharmaceutical and natural product structures, some of which have good biological activities. The Van Leusen [3+2] cycloaddition reaction based on tosylmethyl isocyanides (TosMICs) and electron-deficient compounds as a substrate, which has been continuously developed due to its advantages such as operationally simple, easily available starting materials, and broadly range of substrates, is one of the most convenient methods to synthetize pyrrole heterocycles. In this review, we discuss the different types of two carbon synthons in the Van Leusen pyrrole reaction and give a summary of the progress of these synthesis methods in the past two decades.

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“…[65] In most instances the isonitrile nitrogen becomes embedded within the pyrrole as the aromatic nitrogen.…”

Section: Condensations Leading To Pyrroles and Indolesmentioning

confidence: 99%

Catalytic Isonitrile Insertions and Condensations Initiated by RNC–X Complexation

et al. 2014

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Isonitriles are delicately poised chemical entities capable of being coaxed to react as nucleophiles or electrophiles. Directing this tunable reactivity with metal and non-metal catalysts provides rapid access to a large array of complex nitrogenous structures ideally functionalized for medicinal applications. Isonitrile insertion into transition metal complexes has featured in numerous synthetic and mechanistic studies, leading to rapid deployment of isonitriles in numerous catalytic processes, including multicomponent reactions (MCR). Covering the literature from 1990–2014, the present review collates reaction types to highlight reactivity trends and allow catalyst comparison.

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Synthesis of Pyrroles and Their Derivatives from Isocyanides

Cited by 10 publications

References 176 publications

Radical Nitration-Debromination of α-Bromo-α-fluoroalkenes as a Stereoselective Route to Aromatic α-Fluoronitroalkenes—Functionalized Fluorinated Building Blocks for Organic Synthesis

Radical Nitration-Debromination of α-Bromo-α-fluoroalkenes as a Stereoselective Route to Aromatic α-Fluoronitroalkenes—Functionalized Fluorinated Building Blocks for Organic Synthesis

Synthesis of Multi-Substituted Pyrrole Derivatives Through [3+2] Cycloaddition with Tosylmethyl Isocyanides (TosMICs) and Electron-Deficient Compounds

Catalytic Isonitrile Insertions and Condensations Initiated by RNC–X Complexation

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