A Reinvestigation of 4-Hydroxyindole-6-carboxylate Synthesis from Pyrrole-2-carboxaldehyde: A Facile Synthesis of Indoles and Indolizines
Publication type: Journal Article
Publication date: 2004-09-09
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
15387633
Organic Chemistry
Abstract
Cyclization of the Stobbe product 3 under the literature conditions (acetic anhydride/sodium acetate) affords both the indole 6 and the indolizine 8. The presence of base promotes the formation of indolizine products, and using acetic anhydride/triethylamine leads to indolizine products in good yield. Improved conditions for conversion to indoles 2, 5, and 6 are reported, and inconsistencies in some of the literature structure assignments and characterization data are noted.
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35
Total citations:
35
Citations from 2024:
2
(5.72%)
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GOST
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Kim M., Vedejs E. A Reinvestigation of 4-Hydroxyindole-6-carboxylate Synthesis from Pyrrole-2-carboxaldehyde: A Facile Synthesis of Indoles and Indolizines // Journal of Organic Chemistry. 2004. Vol. 69. No. 20. pp. 6945-6948.
GOST all authors (up to 50)
Copy
Kim M., Vedejs E. A Reinvestigation of 4-Hydroxyindole-6-carboxylate Synthesis from Pyrrole-2-carboxaldehyde: A Facile Synthesis of Indoles and Indolizines // Journal of Organic Chemistry. 2004. Vol. 69. No. 20. pp. 6945-6948.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/jo040191e
UR - https://doi.org/10.1021/jo040191e
TI - A Reinvestigation of 4-Hydroxyindole-6-carboxylate Synthesis from Pyrrole-2-carboxaldehyde: A Facile Synthesis of Indoles and Indolizines
T2 - Journal of Organic Chemistry
AU - Kim, Musong
AU - Vedejs, Edwin
PY - 2004
DA - 2004/09/09
PB - American Chemical Society (ACS)
SP - 6945-6948
IS - 20
VL - 69
PMID - 15387633
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2004_Kim,
author = {Musong Kim and Edwin Vedejs},
title = {A Reinvestigation of 4-Hydroxyindole-6-carboxylate Synthesis from Pyrrole-2-carboxaldehyde: A Facile Synthesis of Indoles and Indolizines},
journal = {Journal of Organic Chemistry},
year = {2004},
volume = {69},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/jo040191e},
number = {20},
pages = {6945--6948},
doi = {10.1021/jo040191e}
}
Cite this
MLA
Copy
Kim, Musong, and Edwin Vedejs. “A Reinvestigation of 4-Hydroxyindole-6-carboxylate Synthesis from Pyrrole-2-carboxaldehyde: A Facile Synthesis of Indoles and Indolizines.” Journal of Organic Chemistry, vol. 69, no. 20, Sep. 2004, pp. 6945-6948. https://doi.org/10.1021/jo040191e.