volume 45 issue 10 pages 1771

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

RH Prager
Chris Tsopelas
Publication typeJournal Article
Publication date1992-01-01
scimago Q3
wos Q4
SJR0.279
CiteScore2.6
Impact factor0.9
ISSN00049425, 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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GOST |
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GOST Copy
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.
GOST all authors (up to 50) Copy
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.
RIS |
Cite this
RIS Copy
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 -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@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}
}
MLA
Cite this
MLA Copy
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.