Details
| Originalsprache | Englisch |
|---|---|
| Seiten (von - bis) | 226-234 |
| Seitenumfang | 9 |
| Fachzeitschrift | European Journal of Organic Chemistry |
| Jahrgang | 2015 |
| Ausgabenummer | 1 |
| Publikationsstatus | Veröffentlicht - 5 Nov. 2014 |
Abstract
Bidirectional reactions are an efficient tool for the synthesis of larger, often symmetric compounds. Whereas the ring opening of benzocyclobutene derivatives with subsequent cycloaddition of the ortho-quinodimethanes formed has been used extensively for the syntheses of various classes of compounds such as steroids, acenes, and natural as well as synthetic oligocycles including heterocyclic systems, the respective bidirectional reactions have barely been explored. Here, the first bidirectional cycloadditions starting from benzo-[1,2:4,5]dicyclobutene derivatives are presented using Nmethylmaleinimide as the dienophile. The benzo[1,2:4,5]-dicyclobutene derivatives used have in common that they are dimethylacetals of the respective diones. As a consequence, the cycloadducts easily undergo elimination of methanol. Subsequent dehydrogenations generate the aromatic anthracene systems, which are part of the benzo[1,2-f:4,5-f′]diisoindole-1,3,7,9-tetraone derivatives formed as the final products.
ASJC Scopus Sachgebiete
- Chemie (insg.)
- Physikalische und Theoretische Chemie
- Chemie (insg.)
- Organische Chemie
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in: European Journal of Organic Chemistry, Jahrgang 2015, Nr. 1, 05.11.2014, S. 226-234.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review
}
TY - JOUR
T1 - The first bidirectional [4+2] cycloadditions of benzo[1,2:4,5]dicyclobutenes
T2 - Synthesis of benzo[1,2-f:4,5-f′]diisoindole-1,3,7,9-tetraones
AU - Abdelhamid, Ismail Abdelshafy
AU - Butenschön, Holger
PY - 2014/11/5
Y1 - 2014/11/5
N2 - Bidirectional reactions are an efficient tool for the synthesis of larger, often symmetric compounds. Whereas the ring opening of benzocyclobutene derivatives with subsequent cycloaddition of the ortho-quinodimethanes formed has been used extensively for the syntheses of various classes of compounds such as steroids, acenes, and natural as well as synthetic oligocycles including heterocyclic systems, the respective bidirectional reactions have barely been explored. Here, the first bidirectional cycloadditions starting from benzo-[1,2:4,5]dicyclobutene derivatives are presented using Nmethylmaleinimide as the dienophile. The benzo[1,2:4,5]-dicyclobutene derivatives used have in common that they are dimethylacetals of the respective diones. As a consequence, the cycloadducts easily undergo elimination of methanol. Subsequent dehydrogenations generate the aromatic anthracene systems, which are part of the benzo[1,2-f:4,5-f′]diisoindole-1,3,7,9-tetraone derivatives formed as the final products.
AB - Bidirectional reactions are an efficient tool for the synthesis of larger, often symmetric compounds. Whereas the ring opening of benzocyclobutene derivatives with subsequent cycloaddition of the ortho-quinodimethanes formed has been used extensively for the syntheses of various classes of compounds such as steroids, acenes, and natural as well as synthetic oligocycles including heterocyclic systems, the respective bidirectional reactions have barely been explored. Here, the first bidirectional cycloadditions starting from benzo-[1,2:4,5]dicyclobutene derivatives are presented using Nmethylmaleinimide as the dienophile. The benzo[1,2:4,5]-dicyclobutene derivatives used have in common that they are dimethylacetals of the respective diones. As a consequence, the cycloadducts easily undergo elimination of methanol. Subsequent dehydrogenations generate the aromatic anthracene systems, which are part of the benzo[1,2-f:4,5-f′]diisoindole-1,3,7,9-tetraone derivatives formed as the final products.
KW - Acetals
KW - Cycloaddition
KW - Nitrogen heterocycles
KW - Reactive intermediates
KW - Ring opening reactions
UR - http://www.scopus.com/inward/record.url?scp=84919683551&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201403247
DO - 10.1002/ejoc.201403247
M3 - Article
AN - SCOPUS:84919683551
VL - 2015
SP - 226
EP - 234
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 1
ER -