Regiochemical Switching in Diels−Alder Cycloadditions by Change in Oxidation State of Removable Diene Sulfur Substituents. Synthesis of Carbazoles by Sequential Heteroannulation and Diels−Alder Cycloaddition
Тип публикации: Journal Article
Дата публикации: 2003-03-18
scimago Q2
wos Q1
БС1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
12688806
Organic Chemistry
Краткое описание
The palladium-catalyzed heteroannulation of N-carbobenzyloxy-o-iodoanilines with 1-phenylthio-1,3-butadiene afforded indolines 7, which were oxidized with DDQ to produce vinylogous 2-(phenylthio)indoles 8. The latter compounds underwent highly regioselective Diels-Alder cycloadditions with methyl propiolate in the presence of MeAlCl(2) or AlCl(3), with simultaneous elimination of benzenethiol, to afford methyl N-(carbobenzyloxy)carbazole-3-carboxylates 9 and, in some cases, the N-deprotected derivatives 11. This is the opposite regiochemistry of that observed previously with the corresponding sulfone analogues of 8. Thus, the regiochemistry of the cycloaddition can be effectively controlled by appropriate choice of oxidation state of the diene sulfur substituent.
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Back T. G., Pandyra A., Wulff J. E. Regiochemical Switching in Diels−Alder Cycloadditions by Change in Oxidation State of Removable Diene Sulfur Substituents. Synthesis of Carbazoles by Sequential Heteroannulation and Diels−Alder Cycloaddition // Journal of Organic Chemistry. 2003. Vol. 68. No. 8. pp. 3299-3302.
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Back T. G., Pandyra A., Wulff J. E. Regiochemical Switching in Diels−Alder Cycloadditions by Change in Oxidation State of Removable Diene Sulfur Substituents. Synthesis of Carbazoles by Sequential Heteroannulation and Diels−Alder Cycloaddition // Journal of Organic Chemistry. 2003. Vol. 68. No. 8. pp. 3299-3302.
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TY - JOUR
DO - 10.1021/jo0268714
UR - https://doi.org/10.1021/jo0268714
TI - Regiochemical Switching in Diels−Alder Cycloadditions by Change in Oxidation State of Removable Diene Sulfur Substituents. Synthesis of Carbazoles by Sequential Heteroannulation and Diels−Alder Cycloaddition
T2 - Journal of Organic Chemistry
AU - Back, Thomas G.
AU - Pandyra, Aleksandra
AU - Wulff, Jeremy E
PY - 2003
DA - 2003/03/18
PB - American Chemical Society (ACS)
SP - 3299-3302
IS - 8
VL - 68
PMID - 12688806
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2003_Back,
author = {Thomas G. Back and Aleksandra Pandyra and Jeremy E Wulff},
title = {Regiochemical Switching in Diels−Alder Cycloadditions by Change in Oxidation State of Removable Diene Sulfur Substituents. Synthesis of Carbazoles by Sequential Heteroannulation and Diels−Alder Cycloaddition},
journal = {Journal of Organic Chemistry},
year = {2003},
volume = {68},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/jo0268714},
number = {8},
pages = {3299--3302},
doi = {10.1021/jo0268714}
}
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Back, Thomas G., et al. “Regiochemical Switching in Diels−Alder Cycloadditions by Change in Oxidation State of Removable Diene Sulfur Substituents. Synthesis of Carbazoles by Sequential Heteroannulation and Diels−Alder Cycloaddition.” Journal of Organic Chemistry, vol. 68, no. 8, Mar. 2003, pp. 3299-3302. https://doi.org/10.1021/jo0268714.