Synthetic Studies towards CH‐Diazomethane Sulfonamides: a Novel Type of Diazo Reagents

Preparation of CH‐diazomethane sulfonamides has been developed for the first time. Their utility as a new type of diazo reagents was showcased in cycloaddition reactions with electron‐deficient alkynes and β‐nitro styrenes which delivered medicinally important pyrazole‐3‐sulfonamides in good to exce...

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Bibliographic Details
Published inEuropean journal of organic chemistry Vol. 2020; no. 27; pp. 4112 - 4115
Main Authors Bubyrev, Andrey, Dar'in, Dmitry, Kantin, Grigory, Krasavin, Mikhail
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 23.07.2020
Wiley Subscription Services, Inc
Subjects
Alkynes
Chemistry
Chemistry, Organic
Cycloaddition
Deacetylation
Diazomethane
Diazomethane sulfonamides
Physical Sciences
Pyrazole
Reagents
SAFE diazo transfer
Science & Technology
Styrenes
Sulfonamides
SAFE diazo transfer
Cycloaddition
Diazomethane sulfonamides
Deacetylation
ALPHA-DIAZOPHOSPHONIC ACIDS
Alkynes
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Summary:Preparation of CH‐diazomethane sulfonamides has been developed for the first time. Their utility as a new type of diazo reagents was showcased in cycloaddition reactions with electron‐deficient alkynes and β‐nitro styrenes which delivered medicinally important pyrazole‐3‐sulfonamides in good to excellent yields. Previously not described CH‐diazomethane sulfonamides have been synthesized from chloroacetone in 5 steps with one chromatographic purification, and gave pyrazoles in cycloaddition reaction with acetylenes.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202000446