Journal of Organic Chemistry, volume 84, issue 7, pages 3743-3753
Synthesis of 1-(2-Aminovinyl)indoles and 1,3′-Biindoles by Reaction of 2,2-Diaryl-Substituted 2H-Azirines with α-Imino Rh(II) Carbenoids
Publication type: Journal Article
Publication date: 2019-01-27
Journal:
Journal of Organic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
An effective and operationally simple method for the preparation of 1-(2-(sulfonamido)vinyl)indoles (SAV-indoles) by the Rh(II)-catalyzed reaction of 2,2-diaryl-2 H-azirines with 1-sulfonyl-1,2,3-triazoles has been developed. This method enables the stereoselective synthesis of a variety of 1,2,3-trisubstituted indoles having a Z configuration of the (1-aryl-2-(sulfonamido)vinyl) substituent. The reaction mechanism, supported by DFT calculations, involves the formation of 1,4-diazahexa-1,3,5-trienes, which rapidly cyclize to 2,2-diaryl-1-sulfonyl-1,2-dihydropyrazines. These compounds can be isolated at an early stage of the reaction, but under prolonged heating they isomerize into 7a H-indolium ylides, followed by a barrierless 1,5-prototropic shift to SAV-indoles. The developed methodology was also applied to the preparation of 1,3'-biindoles from 2,2-diaryl-2 H-azirines using 3-diazoindolin-2-imines instead of 1-sulfonyl-1,2,3-triazoles.
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- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Khaidarov A. R. et al. Synthesis of 1-(2-Aminovinyl)indoles and 1,3′-Biindoles by Reaction of 2,2-Diaryl-Substituted 2H-Azirines with α-Imino Rh(II) Carbenoids // Journal of Organic Chemistry. 2019. Vol. 84. No. 7. pp. 3743-3753.
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Khaidarov A. R., Rostovskii N. V., Zolotarev A. A., Khlebnikov A. F., Novikov M. S. Synthesis of 1-(2-Aminovinyl)indoles and 1,3′-Biindoles by Reaction of 2,2-Diaryl-Substituted 2H-Azirines with α-Imino Rh(II) Carbenoids // Journal of Organic Chemistry. 2019. Vol. 84. No. 7. pp. 3743-3753.
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TY - JOUR
DO - 10.1021/acs.joc.8b03205
UR - https://doi.org/10.1021%2Facs.joc.8b03205
TI - Synthesis of 1-(2-Aminovinyl)indoles and 1,3′-Biindoles by Reaction of 2,2-Diaryl-Substituted 2H-Azirines with α-Imino Rh(II) Carbenoids
T2 - Journal of Organic Chemistry
AU - Khaidarov, Adel R
AU - Rostovskii, Nikolai V
AU - Zolotarev, A. A.
AU - Khlebnikov, Alexander F
AU - Novikov, Mikhail S.
PY - 2019
DA - 2019/01/27 00:00:00
PB - American Chemical Society (ACS)
SP - 3743-3753
IS - 7
VL - 84
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2019_Khaidarov,
author = {Adel R Khaidarov and Nikolai V Rostovskii and A. A. Zolotarev and Alexander F Khlebnikov and Mikhail S. Novikov},
title = {Synthesis of 1-(2-Aminovinyl)indoles and 1,3′-Biindoles by Reaction of 2,2-Diaryl-Substituted 2H-Azirines with α-Imino Rh(II) Carbenoids},
journal = {Journal of Organic Chemistry},
year = {2019},
volume = {84},
publisher = {American Chemical Society (ACS)},
month = {jan},
url = {https://doi.org/10.1021%2Facs.joc.8b03205},
number = {7},
pages = {3743--3753},
doi = {10.1021/acs.joc.8b03205}
}
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Khaidarov, Adel R., et al. “Synthesis of 1-(2-Aminovinyl)indoles and 1,3′-Biindoles by Reaction of 2,2-Diaryl-Substituted 2H-Azirines with α-Imino Rh(II) Carbenoids.” Journal of Organic Chemistry, vol. 84, no. 7, Jan. 2019, pp. 3743-3753. https://doi.org/10.1021%2Facs.joc.8b03205.