One-Pot Synthesis of Multifunctionalized 1-Pyrrolines from 2-Alkyl-2H-azirines and Diazocarbonyl Compounds
Publication type: Journal Article
Publication date: 2022-06-22
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
35732058
Organic Chemistry
Abstract
A novel strategy for the synthesis of 1-pyrrolines based on formal [4 + 1] annulation of 2-alkyl-2H-azirines with diazocarbonyl compounds has been developed. This one-pot approach includes the Rh(II)-catalyzed formation of 4-alkyl-2-azabuta-1,3-dienes, followed by the DBU-promoted cyclization, and features a good substrate tolerance. The 1-pyrrolines containing an ester group at the C3 were prepared in a three-step one-pot procedure starting from 5-alkoxyisoxazoles. The cyclization of 2-azabutadienes to 1-pyrrolines most likely proceeds via the 6π electrocyclization of a conjugated NH-azomethine ylide.
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17
Total citations:
17
Citations from 2024:
13
(76.47%)
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GOST
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Filippov I. et al. One-Pot Synthesis of Multifunctionalized 1-Pyrrolines from 2-Alkyl-2H-azirines and Diazocarbonyl Compounds // Journal of Organic Chemistry. 2022. Vol. 87. No. 13. pp. 8835-8840.
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Filippov I., Novikov M. S., Khlebnikov A. F., Rostovskii N. V. One-Pot Synthesis of Multifunctionalized 1-Pyrrolines from 2-Alkyl-2H-azirines and Diazocarbonyl Compounds // Journal of Organic Chemistry. 2022. Vol. 87. No. 13. pp. 8835-8840.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.joc.2c00977
UR - https://pubs.acs.org/doi/10.1021/acs.joc.2c00977
TI - One-Pot Synthesis of Multifunctionalized 1-Pyrrolines from 2-Alkyl-2H-azirines and Diazocarbonyl Compounds
T2 - Journal of Organic Chemistry
AU - Filippov, Ilya
AU - Novikov, Mikhail S.
AU - Khlebnikov, Alexander F
AU - Rostovskii, Nikolai V
PY - 2022
DA - 2022/06/22
PB - American Chemical Society (ACS)
SP - 8835-8840
IS - 13
VL - 87
PMID - 35732058
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{2022_Filippov,
author = {Ilya Filippov and Mikhail S. Novikov and Alexander F Khlebnikov and Nikolai V Rostovskii},
title = {One-Pot Synthesis of Multifunctionalized 1-Pyrrolines from 2-Alkyl-2H-azirines and Diazocarbonyl Compounds},
journal = {Journal of Organic Chemistry},
year = {2022},
volume = {87},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.2c00977},
number = {13},
pages = {8835--8840},
doi = {10.1021/acs.joc.2c00977}
}
Cite this
MLA
Copy
Filippov, Ilya, et al. “One-Pot Synthesis of Multifunctionalized 1-Pyrrolines from 2-Alkyl-2H-azirines and Diazocarbonyl Compounds.” Journal of Organic Chemistry, vol. 87, no. 13, Jun. 2022, pp. 8835-8840. https://pubs.acs.org/doi/10.1021/acs.joc.2c00977.