β-Chloro-α,β-unsaturated carbonyls as convenient precursors of highly substituted benzenes

The Diels–Alder reactions of three β -chloro- α , β -unsaturated carbonyl compounds 1–3 with different dienes were carried out to afford highly functionalized cyclohexenes 4–9 , bearing quaternary centers, in good yields. These cycloadducts (CAs) undergo dehydrochlorination with subsequent aromatiza...

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Bibliographic Details
Published in:Journal of the Iranian Chemical Society 2018-03, Vol.15 (3), p.629-636
Main Authors: Barhoumi-Slimi, T. M., Ourévitch, M.
Format: Article
Language:English
Subjects:
Analytical Chemistry
Biochemistry
Carbonyl compounds
Carbonyls
Chemistry
Chemistry and Materials Science
Dehydrochlorination
Dienes
Infrared radiation
Inorganic Chemistry
Isomers
NMR
Nuclear magnetic resonance
Organic Chemistry
Original Paper
Physical Chemistry
Precursors
Substitutes
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Summary:The Diels–Alder reactions of three β -chloro- α , β -unsaturated carbonyl compounds 1–3 with different dienes were carried out to afford highly functionalized cyclohexenes 4–9 , bearing quaternary centers, in good yields. These cycloadducts (CAs) undergo dehydrochlorination with subsequent aromatization in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene DBU to produce new substituted benzenes 11–14 . Compound 10 is the product of lactonization and removal of an HCl molecule from compound 7 . All products were characterized by NMR, IR, elementary analysis and some of them by MS. Structure assignments of isomers were carried out on the basis of NMR chemical shifts and coupling constants using 1D, 2D and heteronOe NMR techniques.
ISSN:1735-207X
1735-2428
DOI:10.1007/s13738-017-1263-1