Alkyne–thiocarbonyl metathesis instead of Diels–Alder addition: Coupling of thiopyrano[4,3-b]indole-3(5H)-thiones and dimethyl acetylenedicarboxylate
Publication type: Journal Article
Publication date: 2022-04-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
The cascade reaction of thiopyrano[4,3- b ]indole-3(5 H )-thiones and dimethyl acetylenedicarboxylate (DMAD) was found. The mechanism has been investigated in detail by DFT PCM/B3LYP/6–311++G(d,p) quantum chemical calculations. Initially, the reaction occurs via an alkyne–thiocarbonyl metathesis mechanism. At the next stages, unprecedented rearrangement takes place: thiopyrane ring opening and thiophene ring closure proceed. Cycloaddition of intermediate thioketone and a second equivalent of DMAD leads to the resulting thiopyrano[4,3- b ]indole derivative bearing thienyl substituent.
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Suzdalev K. F. et al. Alkyne–thiocarbonyl metathesis instead of Diels–Alder addition: Coupling of thiopyrano[4,3-b]indole-3(5H)-thiones and dimethyl acetylenedicarboxylate // Tetrahedron. 2022. Vol. 112. p. 132751.
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Suzdalev K. F., Vyalyh J. V., Tkachev V. V., Burov O. N., Lisovin A. V., Kletskii M. E., Borodkin G. S., Kurbatov S. V., Lysenko E. A. Alkyne–thiocarbonyl metathesis instead of Diels–Alder addition: Coupling of thiopyrano[4,3-b]indole-3(5H)-thiones and dimethyl acetylenedicarboxylate // Tetrahedron. 2022. Vol. 112. p. 132751.
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TY - JOUR
DO - 10.1016/j.tet.2022.132751
UR - https://doi.org/10.1016/j.tet.2022.132751
TI - Alkyne–thiocarbonyl metathesis instead of Diels–Alder addition: Coupling of thiopyrano[4,3-b]indole-3(5H)-thiones and dimethyl acetylenedicarboxylate
T2 - Tetrahedron
AU - Suzdalev, K F
AU - Vyalyh, J V
AU - Tkachev, V V
AU - Burov, O N
AU - Lisovin, A V
AU - Kletskii, M E
AU - Borodkin, G S
AU - Kurbatov, S V
AU - Lysenko, E A
PY - 2022
DA - 2022/04/01
PB - Elsevier
SP - 132751
VL - 112
SN - 0040-4020
SN - 1464-5416
ER -
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@article{2022_Suzdalev,
author = {K F Suzdalev and J V Vyalyh and V V Tkachev and O N Burov and A V Lisovin and M E Kletskii and G S Borodkin and S V Kurbatov and E A Lysenko},
title = {Alkyne–thiocarbonyl metathesis instead of Diels–Alder addition: Coupling of thiopyrano[4,3-b]indole-3(5H)-thiones and dimethyl acetylenedicarboxylate},
journal = {Tetrahedron},
year = {2022},
volume = {112},
publisher = {Elsevier},
month = {apr},
url = {https://doi.org/10.1016/j.tet.2022.132751},
pages = {132751},
doi = {10.1016/j.tet.2022.132751}
}