Reactions of dipivaloylketene and its dimer with NH(2)-nucleophiles. Formation of amides, hydrazides, ureides and pyrimidine-2,4-diones

Kollenz, Gert, Kappe, C. Oliver, Dalvi, Turkaram S. and Wentrup, Curt (2001) Reactions of dipivaloylketene and its dimer with NH(2)-nucleophiles. Formation of amides, hydrazides, ureides and pyrimidine-2,4-diones. Arkivoc, 2001 vi: 30-41. doi:10.3998/ark.5550190.0002.603


Author Kollenz, Gert
Kappe, C. Oliver
Dalvi, Turkaram S.
Wentrup, Curt
Title Reactions of dipivaloylketene and its dimer with NH(2)-nucleophiles. Formation of amides, hydrazides, ureides and pyrimidine-2,4-diones
Formatted title
Reactions of dipivaloylketene and its dimer with NH2-nucleophiles. Formation of amides, hydrazides, ureides and pyrimidine-2,4-diones
Journal name Arkivoc
ISSN 1551-7004
1551-7012
1424-6376
Publication date 2001-03-11
Sub-type Article (original research)
DOI 10.3998/ark.5550190.0002.603
Open Access Status DOI
Volume 2001
Issue vi
Start page 30
End page 41
Total pages 12
Place of publication Gainesville, FL, USA
Publisher Arkat USA
Language eng
Subject CX
250303 Physical Organic Chemistry
780103 Chemical sciences
Formatted abstract
Dipivaloylketene 1 and its dimer 2 add several NH2-nucleophiles affording the open-chain dipivaloylacetic acid derivatives 3, 5, 6, 9 and 10. With methylhydrazine as well as 2,6-dimethylaniline the 2:1 products 8 and 11, respectively, are formed. The tetracarbonyl compounds 3a-c only undergo PPA-induced cyclocondensation, and with concomitant loss of one pivaloyl group the pyrimidine-2,4-diones 4a-c are obtained.
Keyword Dipivaloylketene
NH2 nucleophiles
Amides
Hydrazides
Ureides
Pyrimidine-2,4-diones
Cyclocondensation
Q-Index Code CX
Q-Index Status Provisional Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collection: School of Chemistry and Molecular Biosciences
 
Versions
Version Filter Type
Citation counts: Scopus Citation Count Cited 2 times in Scopus Article | Citations
Google Scholar Search Google Scholar
Created: Wed, 15 Aug 2007, 01:30:37 EST