Knoevenagel Reactions of 6,7-Dihydropyrrolo[2,3-c]azepine-4,8(1H,5H)-dione: An Approach to the Synthesis of Pyrrolic Marine Natural Products
Publication type: Journal Article
Publication date: 1992-01-01
scimago Q3
wos Q4
SJR: 0.279
CiteScore: 2.6
Impact factor: 0.9
ISSN: 00049425, 14450038
General Chemistry
Abstract
The title compound undergoes reaction with diethyl malonate or ethyl hydrogen malonate in the presence of TiCl4 to give a mixture of endocyclic and exocyclic products, (5) and (6) or (13) and (14). The latter compounds have been decarboxylated and brominated to give the allylic bromide (18). Model experiments to substitute the bromine with amines suggest this compound would prove to be only a mediocre intermediate for the synthesis of the pyrrolic guanidine (2) found in Phakellia flabellata .
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Prager R., Tsopelas C. Knoevenagel Reactions of 6,7-Dihydropyrrolo[2,3-c]azepine-4,8(1H,5H)-dione: An Approach to the Synthesis of Pyrrolic Marine Natural Products // Australian Journal of Chemistry. 1992. Vol. 45. No. 10. p. 1771.
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Prager R., Tsopelas C. Knoevenagel Reactions of 6,7-Dihydropyrrolo[2,3-c]azepine-4,8(1H,5H)-dione: An Approach to the Synthesis of Pyrrolic Marine Natural Products // Australian Journal of Chemistry. 1992. Vol. 45. No. 10. p. 1771.
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RIS
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TY - JOUR
DO - 10.1071/CH9921771
UR - https://doi.org/10.1071/CH9921771
TI - Knoevenagel Reactions of 6,7-Dihydropyrrolo[2,3-c]azepine-4,8(1H,5H)-dione: An Approach to the Synthesis of Pyrrolic Marine Natural Products
T2 - Australian Journal of Chemistry
AU - Prager, RH
AU - Tsopelas, Chris
PY - 1992
DA - 1992/01/01
PB - CSIRO Publishing
SP - 1771
IS - 10
VL - 45
SN - 0004-9425
SN - 1445-0038
ER -
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BibTex (up to 50 authors)
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@article{1992_Prager,
author = {RH Prager and Chris Tsopelas},
title = {Knoevenagel Reactions of 6,7-Dihydropyrrolo[2,3-c]azepine-4,8(1H,5H)-dione: An Approach to the Synthesis of Pyrrolic Marine Natural Products},
journal = {Australian Journal of Chemistry},
year = {1992},
volume = {45},
publisher = {CSIRO Publishing},
month = {jan},
url = {https://doi.org/10.1071/CH9921771},
number = {10},
pages = {1771},
doi = {10.1071/CH9921771}
}
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MLA
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Prager, RH, and Chris Tsopelas. “Knoevenagel Reactions of 6,7-Dihydropyrrolo[2,3-c]azepine-4,8(1H,5H)-dione: An Approach to the Synthesis of Pyrrolic Marine Natural Products.” Australian Journal of Chemistry, vol. 45, no. 10, Jan. 1992, p. 1771. https://doi.org/10.1071/CH9921771.