Experimental and Theoretical Investigation of the Coarctate Cyclization of (2-Ethynylphenyl)phenyldiazenes
Тип публикации: Journal Article
Дата публикации: 2004-09-17
SCImago Q2
WOS Q1
БС1
SJR: 0.604
CiteScore: 5.8
Impact factor: 3.3
ISSN: 00223263, 15206904
PubMed ID:
15471442
Organic Chemistry
Краткое описание
A new route to substituted 2-phenyl-2H-indazoles through the cyclization of (2-ethynylphenyl)phenyldiazenes is presented. A coarctate reaction pathway forms the isoindazole carbene under neutral conditions, at moderate temperatures, and without the requirement of a carbene stabilizer. A wide variety of previously unknown diazene precursors was synthesized and cyclized. Trapping of the carbene with a silyl alcohol followed by deprotection affords the 3-hydroxymethyl-2-phenyl-2H-indazoles in good overall yield. The free carbene could also be trapped as a [2 + 1] cycloadduct with 2,3-dimethyl-2-butene.
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Shirtcliff L. D. et al. Experimental and Theoretical Investigation of the Coarctate Cyclization of (2-Ethynylphenyl)phenyldiazenes // Journal of Organic Chemistry. 2004. Vol. 69. No. 21. pp. 6979-6985.
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Shirtcliff L. D. Experimental and Theoretical Investigation of the Coarctate Cyclization of (2-Ethynylphenyl)phenyldiazenes // Journal of Organic Chemistry. 2004. Vol. 69. No. 21. pp. 6979-6985.
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TY - JOUR
DO - 10.1021/jo049011r
UR - https://doi.org/10.1021/jo049011r
TI - Experimental and Theoretical Investigation of the Coarctate Cyclization of (2-Ethynylphenyl)phenyldiazenes
T2 - Journal of Organic Chemistry
AU - Shirtcliff, Laura D.
PY - 2004
DA - 2004/09/17
PB - American Chemical Society (ACS)
SP - 6979-6985
IS - 21
VL - 69
PMID - 15471442
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2004_Shirtcliff,
author = {Laura D. Shirtcliff},
title = {Experimental and Theoretical Investigation of the Coarctate Cyclization of (2-Ethynylphenyl)phenyldiazenes},
journal = {Journal of Organic Chemistry},
year = {2004},
volume = {69},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/jo049011r},
number = {21},
pages = {6979--6985},
doi = {10.1021/jo049011r}
}
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MLA
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Shirtcliff, Laura D., et al. “Experimental and Theoretical Investigation of the Coarctate Cyclization of (2-Ethynylphenyl)phenyldiazenes.” Journal of Organic Chemistry, vol. 69, no. 21, Sep. 2004, pp. 6979-6985. https://doi.org/10.1021/jo049011r.
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