Annulation of 1H-pyrrole-2,3-diones by thioacetamide: an approach to 5-azaisatins

A novel approach to 1H-pyrrolo[3,2-c]pyridine-2,3-diones (5-azaisatins) has been developed via an unprecedented annulation of pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones by thioacetamide. A new way of C–H functionalization of thioacetamide has been discovered. The reaction proceeds under green cata...

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Published inBeilstein journal of organic chemistry Vol. 15; no. 1; pp. 364 - 370
Main Authors Kobelev, Aleksandr I, Stepanova, Ekaterina E, Dmitriev, Maksim V, Maslivets, Andrey N
Format Journal Article
LanguageEnglish
Published Frankfurt am Main Beilstein-Institut zur Föerderung der Chemischen Wissenschaften 07.02.2019
Beilstein-Institut
Subjects
annulation
Chemistry
domino reactions
Experiments
Full Research Paper
isatin
nitrogen heterocycles
Pyridines
Solvents
Temperature effects
Thioacetamide
thioamides
Russia
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Summary:A novel approach to 1H-pyrrolo[3,2-c]pyridine-2,3-diones (5-azaisatins) has been developed via an unprecedented annulation of pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones by thioacetamide. A new way of C–H functionalization of thioacetamide has been discovered. The reaction proceeds under green catalyst-free conditions.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:2195-951X
1860-5397
1860-5397
DOI:10.3762/bjoc.15.32