Metal-free, base promoted sp2 C–H functionalization in the sulfonamidation of 1,4-naphthoquinones
Literature Information
Publication Date
2018-06-30
DOI
10.1039/C8OB00818C
Impact Factor
3.876
Authors
Ramanathan Devenderan
View Original
Abstract
A novel, metal-free, base promoted sp2 C–H functionalization in the sulfonamidation of 1,4-naphthoquinones via a [3 + 2] cycloaddition reaction using sulfonyl azides under mild reaction conditions is reported. In this straightforward atom- and step-economical protocol, the active alkene moiety of quinone undergoes a thermal azide–alkene [3 + 2] cycloaddition followed by proton abstraction, ring opening and elimination of a nitrogen molecule to form sulfonamidation products in good yield and all the synthesized sulfonamidation derivatives exhibit good absorption and emission characteristics. In addition, the electrochemical properties of both 1,4-naphthoquinone and menadione sulfonamidation derivatives are studied and significant redox potentials are observed. Other important features of this methodology are readily accessible and easy to handle starting materials, milder conditions, reaction with a wide range of substrates and shorter reaction times with good yields.
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Source Journal
Organic & Biomolecular Chemistry
CiteScore:
3.4
Self-citation Rate:
10.3%
Articles per Year:
1041
Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.
Recommended Compounds
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S-[2,3-Bis(palmitoyloxy)propyl]-N-[(9H-fluoren-9-ylmethoxy)(hydroxy)methylene]cysteine
CAS Number:
210532-98-2
Molecular Formula:
C53H83NO8S
![(2E)-3-(3-Chlorophenyl)-N-{2-[4-(methylsulfonyl)-1-piperazinyl]-2-oxoethyl}acrylamide structure](https://static.chemtradehub.com/structs/250/2505001-54-5-c1e9.webp "(2E)-3-(3-Chlorophenyl)-N-{2-[4-(methylsulfonyl)-1-piperazinyl]-2-oxoethyl}acrylamide structure")
(2E)-3-(3-Chlorophenyl)-N-{2-[4-(methylsulfonyl)-1-piperazinyl]-2-oxoethyl}acrylamide
CAS Number:
2505001-54-5
Molecular Formula:
C16H20ClN3O4S
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