3,5‐Dihydro‐2<i>H</i>‐thieno[2,3‐<i>c</i>]pyrrole 1,1‐Dioxide – A New Simple Pyrrole Unit. Preliminary Communication

Banala, Srinivas; Wurst, Klaus; Kräutler, Bernhard

doi:10.1002/hlca.200900362

Cited by 8 publications

(1 citation statement)

References 31 publications

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“…18 In many cases, these substrates are useful precursors to the corresponding 1,3-dienes, allowing for the traceless installation of a fused-heteroaromatic function. 18 In 2010, Banala and Kräutler reported the synthesis of 3,5-dihydro-2H-thieno[2,3-c]pyrrole-1,1-dioxide (138); 65 the corresponding regioisomer (142, 3,5-dihydro-1H-thie-no[3,4-c]pyrrole-2,2-dioxide) had previously been reported by Takayama and co-workers and was prepared from 3,4bis(bromomethyl)-3-sulfolene (Scheme 36). 66 In 2000, the Kräutler group used 142 in a synthesis of tetrasulfolenoporphyrin 143.…”

Section: Heteroaromatic Bicyclic Sulfolenesmentioning

confidence: 99%

3-Sulfolenes and Their Derivatives: Synthesis and Applications

Brant

Wulff

2015

Synthesis

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The diverse substitution patterns available to 3-sulfolenes have long made them useful for the preparation of multi-substituted 1,3-diene equivalents. More recently, the 3-sulfolene motif itself (or its reduced sulfolane congener) is finding increasing application as a structural element in the creation of molecules for biological applications. This review describes various methods to afford 3-sulfolene building blocks and their derivatives. Selected applications in synthetic and medicinal chemistry are also discussed. 1 Introduction 2 The Preparation of Monocyclic Sulfolene Building Blocks 2.1 Sulfolenes through Electrophilic Addition 2.1.1 Sulfolenes through Nucleophilic Addition to 4-Bromo-2-sulfolene 2.2 Sulfolenes through Oxidation of a Thiol Precursor 2.3 Sulfolenes through Noble Metal Catalysis 2.4 Sulfolenes through Deprotonation Followed by Alkylation 3 Synthesis of Bicyclic Sulfolenes and Their Derivatives 3.

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Section: Heteroaromatic Bicyclic Sulfolenesmentioning

confidence: 99%

3-Sulfolenes and Their Derivatives: Synthesis and Applications

Brant

Wulff

2015

Synthesis

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A Dipyrrin Programmed for Covalent Loading with Fullerenes

Wurst

Kräutler

2018

Chemistry A European J

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We describe here a di‐(β,β′‐sulfoleno)pyrrin programmed for efficient and specific β,β′‐functionalization via [4+2] cycloaddition reactions. At 120 °C and in the presence of an excess of C60‐fullerene the di‐(β,β′‐sulfoleno)pyrrin decomposed cleanly, furnishing a di‐(β,β′‐fullereno)pyrrin and the corresponding monofullereno‐dipyrrin in an overall yield of 96 %. Hence, relatively mild thermolysis of the di‐(β,β′‐sulfoleno)pyrrin induced stepwise extrusion of two equivalents of SO2, producing highly reactive dipyrrin‐β,β′‐diene intermediates readily, providing a very effective path to [4+2]‐cycloadducts. As presented here by the example of the covalent attachment of C60‐fullerene units, a convenient general methodology for the efficient synthesis of covalent dipyrrin β,β′‐cycloadducts is made available.

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Copper(II)‐Catalyzed [4+1] Annulation of Propargylamines with N,O‐Acetals: Entry to the Synthesis of Polysubstituted Pyrrole Derivatives

2015

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Described herein is the CuCl2‐catalyzed [4+1] annulation of a variety of propargylamines with N,O‐acetals that function as a C1 unit, leading to the production of polysubstituted pyrrole derivatives. Three important features of the N,O‐acetal during the [4+1] annulation series via 5‐endo‐dig cyclization are described: an enolizable substituent adjacent to the central sp3‐carbon is required, the central sp3‐carbon displays the functions of both an electrophile and a nucleophile, and liberation of the secondary amine smoothly leads to the aromatization.

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3,5‐Dihydro‐2H‐thieno[2,3‐c]pyrrole 1,1‐Dioxide – A New Simple Pyrrole Unit. Preliminary Communication

Cited by 8 publications

References 31 publications

3-Sulfolenes and Their Derivatives: Synthesis and Applications

3-Sulfolenes and Their Derivatives: Synthesis and Applications

A Dipyrrin Programmed for Covalent Loading with Fullerenes

Copper(II)‐Catalyzed [4+1] Annulation of Propargylamines with N,O‐Acetals: Entry to the Synthesis of Polysubstituted Pyrrole Derivatives

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