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Novel chromeno[2,3-c]pyrroles synthesized via intramolecular rhodium(ii) carbene trapping

Evgeny Gennadievich Chupakhin 1, 2
Evgeny Gennadievich Chupakhin
Grigoriy Pavlovich Kantin 2
Grigoriy Pavlovich Kantin
Dmitry Viktorovich Dar’in 2
Dmitry Viktorovich Dar’in
Mikhail Yur'evich Krasavin 1, 2
Mikhail Yur'evich Krasavin
Published 2022-04-29
CommunicationVolume 32, Issue 3, 382-383
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Chupakhin E. G. et al. Novel chromeno[2,3-c]pyrroles synthesized via intramolecular rhodium(ii) carbene trapping // Mendeleev Communications. 2022. Vol. 32. No. 3. pp. 382-383.
GOST all authors (up to 50) Copy
Chupakhin E. G., Kantin G. P., Dar’in D. V., Krasavin M. Y. Novel chromeno[2,3-c]pyrroles synthesized via intramolecular rhodium(ii) carbene trapping // Mendeleev Communications. 2022. Vol. 32. No. 3. pp. 382-383.
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TY - JOUR
DO - 10.1016/j.mencom.2022.05.030
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.05.030
TI - Novel chromeno[2,3-c]pyrroles synthesized via intramolecular rhodium(ii) carbene trapping
T2 - Mendeleev Communications
AU - Chupakhin, Evgeny Gennadievich
AU - Kantin, Grigoriy Pavlovich
AU - Dar’in, Dmitry Viktorovich
AU - Krasavin, Mikhail Yur'evich
PY - 2022
DA - 2022/04/29
PB - Mendeleev Communications
SP - 382-383
IS - 3
VL - 32
ER -
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@article{2022_Chupakhin,
author = {Evgeny Gennadievich Chupakhin and Grigoriy Pavlovich Kantin and Dmitry Viktorovich Dar’in and Mikhail Yur'evich Krasavin},
title = {Novel chromeno[2,3-c]pyrroles synthesized via intramolecular rhodium(ii) carbene trapping},
journal = {Mendeleev Communications},
year = {2022},
volume = {32},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.05.030},
number = {3},
pages = {382--383},
doi = {10.1016/j.mencom.2022.05.030}
}
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Chupakhin, Evgeny Gennadievich, et al. “Novel chromeno[2,3-c]pyrroles synthesized via intramolecular rhodium(ii) carbene trapping.” Mendeleev Communications, vol. 32, no. 3, Apr. 2022, pp. 382-383. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.05.030.

Keywords

2H-chromenes
5-diones
chromeno[2,3-c]pyrroles
intramolecular O-H insertion
pyrrolidine-2
rhodium(u) complexes
α-diazo carbonyl compounds

Abstract

Rhodium(ii) carbenes generated from (E)-3-diazo-4-(2-hydroxybenzylidene)-1-phenylpyrrolidine-2,5-dione under- went a facile transformation into novel succinimide-fused 2H-chromenes, chromeno[2,3-c]pyrrole-1,3(2H,3aH)-diones. The process presumably involves an intramolecular O-H insertion reaction.

References

2.
Novel chromene derivatives as TNF-α inhibitors
Cheng J., Ishikawa A., Ono Y., Arrhenius T., Nadzan A.
Bioorganic and Medicinal Chemistry Letters, 2003
3.
Candenatenins A−F, Phenolic Compounds from the Heartwood of Dalbergia candenatensis
Cheenpracha S., Karalai C., Ponglimanont C., Kanjana-Opas A.
Journal of Natural Products, 2009
4.
B. Chen, R. A. Fairhurst, A. Floersheimer, P. Furet, S. Jiang, W. Lu, T. H. Marsilje and A. Vaupel, Patent WO 201164211A1, 2011.
5.
An unusual isopropenyldihydrofuran biflavanol from Tephrosia crassifolia
Gómez-Garibay F., Calderón J.S., De La O Arciniega M., Céspedes C.L., Téllez-Valdés O., Taboada J.
Phytochemistry, 1999
6.
Synthesis and Pharmacological Characterization of Novel 6-Fluorochroman Derivatives as Potential 5-HT1A Receptor Antagonists
Yasunaga T., Kimura T., Naito R., Kontani T., Wanibuchi F., Yamashita H., Nomura T., Tsukamoto S., Yamaguchi T., Mase T.
Journal of Medicinal Chemistry, 1998
7.
Synthesis and structure–activity relationships of analogs of EM-652 (acolbifene), a pure selective estrogen receptor modulator. Study of nitrogen substitution
Gauthier S., Cloutier J., Dory Y.L., Favre A., Mailhot J., Ouellet C., Schwerdtfeger A., Mérand Y., Martel C., Simard J., Labrie F.
Journal of Enzyme Inhibition and Medicinal Chemistry, 2005
8.
Green tea and skin cancer: photoimmunology, angiogenesis and DNA repair
KATIYAR S., ELMETS C., KATIYAR S.
Journal of Nutritional Biochemistry, 2007
10.
Atropisomeric Myristinins:  Selective COX-2 Inhibitors and Antifungal Agents from Myristica cinnamomea
Sawadjoon S., Kittakoop P., Kirtikara K., Vichai V., Tanticharoen M., Thebtaranonth Y.
Journal of Organic Chemistry, 2002
11.
Catalytic Synthesis of 2H-Chromenes
Majumdar N., Paul N.D., Mandal S., de Bruin B., Wulff W.D.
ACS Catalysis, 2015
12.
Chemistry of Heterocyclic Compounds: Chromenes, Chromanones, and Chromones, ed. G. P. Ellis, Wiley, New York, 2009, vol. 31.
13.
Fluorescent probes on the basis of coumarin derivatives for determining biogenic thiols and thiophenols
Bugaenko D.I., Karchava A.V., Yunusova Z.A., Yurovskaya M.A.
Chemistry of Heterocyclic Compounds, 2019
15.
Multicomponent design of chromeno[2,3-b]pyridine systems
Elinson M.N., Ryzhkova Y.E., Ryzhkov F.V.
Russian Chemical Reviews, 2021
16.
Privileged scaffolds for library design and drug discovery
Welsch M.E., Snyder S.A., Stockwell B.R.
Current Opinion in Chemical Biology, 2010
17.
Spirocyclizations Involving Oxonium Ylides Derived from Cyclic α-Diazocarbonyl Compounds: An Entry into 6-Oxa-2-azaspiro[4.5]decane Scaffold.
Dar’in D., Kantin G., Bakulina O., Inyutina A., Chupakhin E., Krasavin M.
Journal of Organic Chemistry, 2020
18.
Chupakhin E.G., Kantin G.P., Dar’in D.V., Krasavin M.
Mendeleev Communications, 2021