TfOH-Catalyzed One-Pot Domino Reaction for Diastereoselective Synthesis of Polysubstituted Tetrahydrospiro[carbazole-1,3′-indoline]s
Publication type: Journal Article
Publication date: 2017-11-27
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
29131626
Organic Chemistry
Abstract
TfOH-catalyzed one-pot sequential reaction of indoles, acetophenones (cyclic ketones), and various 3-methyleneoxindolines in toluene afforded polysubstituted tetrahydrospiro[carbazole-1,3'-indoline]s in satisfactory yields. 1H NMR spectra and single-crystal structures indicated that the obtained tetrahydrospiro[carbazole-1,3'-indoline]s existing in an unusual trans-configuration. The reaction mechanism was believed to proceed with domino acid-catalyzed 3-alkenylation of indoles with acetophenones, Diels-Alder reaction of 3-alkyenylindoles with 3-methyleneoxindolines, and an acid-catalyzed diastereoisomerization process.
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GOST
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Yang R. Y. et al. TfOH-Catalyzed One-Pot Domino Reaction for Diastereoselective Synthesis of Polysubstituted Tetrahydrospiro[carbazole-1,3′-indoline]s // Journal of Organic Chemistry. 2017. Vol. 82. No. 24. pp. 13277-13287.
GOST all authors (up to 50)
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Yang R. Y., Sun J., Yao T., Sun Q., Yan C. TfOH-Catalyzed One-Pot Domino Reaction for Diastereoselective Synthesis of Polysubstituted Tetrahydrospiro[carbazole-1,3′-indoline]s // Journal of Organic Chemistry. 2017. Vol. 82. No. 24. pp. 13277-13287.
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RIS
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TY - JOUR
DO - 10.1021/acs.joc.7b02397
UR - https://doi.org/10.1021/acs.joc.7b02397
TI - TfOH-Catalyzed One-Pot Domino Reaction for Diastereoselective Synthesis of Polysubstituted Tetrahydrospiro[carbazole-1,3′-indoline]s
T2 - Journal of Organic Chemistry
AU - Yang, Ren Yin
AU - Sun, Jing
AU - Yao, Tao
AU - Sun, Qiu
AU - Yan, Chaoguo
PY - 2017
DA - 2017/11/27
PB - American Chemical Society (ACS)
SP - 13277-13287
IS - 24
VL - 82
PMID - 29131626
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2017_Yang,
author = {Ren Yin Yang and Jing Sun and Tao Yao and Qiu Sun and Chaoguo Yan},
title = {TfOH-Catalyzed One-Pot Domino Reaction for Diastereoselective Synthesis of Polysubstituted Tetrahydrospiro[carbazole-1,3′-indoline]s},
journal = {Journal of Organic Chemistry},
year = {2017},
volume = {82},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021/acs.joc.7b02397},
number = {24},
pages = {13277--13287},
doi = {10.1021/acs.joc.7b02397}
}
Cite this
MLA
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Yang, Ren Yin, et al. “TfOH-Catalyzed One-Pot Domino Reaction for Diastereoselective Synthesis of Polysubstituted Tetrahydrospiro[carbazole-1,3′-indoline]s.” Journal of Organic Chemistry, vol. 82, no. 24, Nov. 2017, pp. 13277-13287. https://doi.org/10.1021/acs.joc.7b02397.