Synthesis of Acetylenic Amides with Propyllactam Moieties by In Situ DBU or DBN Ring-Opening Rearrangement in the Presence of Acetylenic Esters
Publication type: Journal Article
Publication date: 2017-12-07
scimago Q2
wos Q2
SJR: 0.559
CiteScore: 4.6
Impact factor: 2.3
ISSN: 00397881, 1437210X
Catalysis
Organic Chemistry
Abstract
DBN (1,5-diazabicyclo[4.3.0]non-5-ene) and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) react with methyl esters of acetylenic acids and excess water (the reactant molar ratio 1:1, in aqueous MeCN, at 20–25 °C, for 48 h) to afford acetylenic amides with pyrrolidone and caprolactam moieties in 89–100% yields. The synthesis involves amines formed in situ from the cyclic amidines, which further react with acetylenic esters.
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Shemyakina O. A. et al. Synthesis of Acetylenic Amides with Propyllactam Moieties by In Situ DBU or DBN Ring-Opening Rearrangement in the Presence of Acetylenic Esters // Synthesis. 2017. Vol. 50. No. 04. pp. 853-858.
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Shemyakina O. A., Shemyakina O., Stepanov A., Stepanov A., Ushakov I., Trofimov B. A. Synthesis of Acetylenic Amides with Propyllactam Moieties by In Situ DBU or DBN Ring-Opening Rearrangement in the Presence of Acetylenic Esters // Synthesis. 2017. Vol. 50. No. 04. pp. 853-858.
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RIS
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TY - JOUR
DO - 10.1055/s-0036-1591852
UR - https://doi.org/10.1055/s-0036-1591852
TI - Synthesis of Acetylenic Amides with Propyllactam Moieties by In Situ DBU or DBN Ring-Opening Rearrangement in the Presence of Acetylenic Esters
T2 - Synthesis
AU - Shemyakina, Olesya A
AU - Shemyakina, Olesya
AU - Stepanov, A.M
AU - Stepanov, Anton
AU - Ushakov, Igor
AU - Trofimov, B. A.
PY - 2017
DA - 2017/12/07
PB - Georg Thieme Verlag KG
SP - 853-858
IS - 04
VL - 50
SN - 0039-7881
SN - 1437-210X
ER -
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@article{2017_Shemyakina,
author = {Olesya A Shemyakina and Olesya Shemyakina and A.M Stepanov and Anton Stepanov and Igor Ushakov and B. A. Trofimov},
title = {Synthesis of Acetylenic Amides with Propyllactam Moieties by In Situ DBU or DBN Ring-Opening Rearrangement in the Presence of Acetylenic Esters},
journal = {Synthesis},
year = {2017},
volume = {50},
publisher = {Georg Thieme Verlag KG},
month = {dec},
url = {https://doi.org/10.1055/s-0036-1591852},
number = {04},
pages = {853--858},
doi = {10.1055/s-0036-1591852}
}
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MLA
Copy
Shemyakina, Olesya A., et al. “Synthesis of Acetylenic Amides with Propyllactam Moieties by In Situ DBU or DBN Ring-Opening Rearrangement in the Presence of Acetylenic Esters.” Synthesis, vol. 50, no. 04, Dec. 2017, pp. 853-858. https://doi.org/10.1055/s-0036-1591852.
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