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Synthesis of 3-acylindolizines based on β-nitro-substituted benzochromenes and carbonyl-stabilized pyridinium ylides

Dmitry Vladimirovich Osipov 1
Dmitry Vladimirovich Osipov
, 
Daria A Rashchepkina 1
Daria A Rashchepkina
, 
Pavel E Krasnikov 1
Pavel E Krasnikov
, 
Vitaly Aleksandrovich Osyanin 1
Vitaly Aleksandrovich Osyanin
1 Samara State Technical University, 443100 Samara, Russian Federation
10.71267/mencom.7789
Published 2025-10-21
Communication , Volume 35, Issue 6, 729-731
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Osipov D. V. et al. Synthesis of 3-acylindolizines based on β-nitro-substituted benzochromenes and carbonyl-stabilized pyridinium ylides // Mendeleev Communications. 2025. Vol. 35. No. 6. pp. 729-731.
GOST all authors (up to 50) Copy
Osipov D. V., Rashchepkina D. A., Krasnikov P. E., Osyanin V. A. Synthesis of 3-acylindolizines based on β-nitro-substituted benzochromenes and carbonyl-stabilized pyridinium ylides // Mendeleev Communications. 2025. Vol. 35. No. 6. pp. 729-731.
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TY - JOUR
DO - 10.71267/mencom.7789
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7789
TI - Synthesis of 3-acylindolizines based on β-nitro-substituted benzochromenes and carbonyl-stabilized pyridinium ylides
T2 - Mendeleev Communications
AU - Osipov, Dmitry Vladimirovich
AU - Rashchepkina, Daria A
AU - Krasnikov, Pavel E
AU - Osyanin, Vitaly Aleksandrovich
PY - 2025
DA - 2025/10/21
PB - Mendeleev Communications
SP - 729-731
IS - 6
VL - 35
ER -
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@article{2025_Osipov,
author = {Dmitry Vladimirovich Osipov and Daria A Rashchepkina and Pavel E Krasnikov and Vitaly Aleksandrovich Osyanin},
title = {Synthesis of 3-acylindolizines based on β-nitro-substituted benzochromenes and carbonyl-stabilized pyridinium ylides},
journal = {Mendeleev Communications},
year = {2025},
volume = {35},
publisher = {Mendeleev Communications},
month = {Oct},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7789},
number = {6},
pages = {729--731},
doi = {10.71267/mencom.7789}
}
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Osipov, Dmitry Vladimirovich, et al. “Synthesis of 3-acylindolizines based on β-nitro-substituted benzochromenes and carbonyl-stabilized pyridinium ylides.” Mendeleev Communications, vol. 35, no. 6, Oct. 2025, pp. 729-731. https://mendcomm.colab.ws/publications/10.71267/mencom.7789.

Keywords

2-nitro-1H-benzochromenes
3-nitro-4H-benzo[h]chromene
indolizines
Michael reaction
pyridinium ylides

Abstract

3-Acylindolizines containing a (1-hydroxynaphthalen-2-yl)methyl substituent at position 1 were obtained via the reaction of 2-nitro-1H-benzochromenes or 3-nitro-4Hbenzo[h]chromene with carbonyl-stabilized pyridinium ylides. The proposed reaction mechanism includes the Michael addition of the pyridinium ylide, opening of the dihydropyran ring, 5-endo-trig cyclization, and elimination of nitrous acid.

Funders

Russian Science Foundation
22-73-10104