Organic Superbases in Annulation with Propargylic Alcohols: Straightforward Synthesis of the Functionalized Oxazolopyrrolohexahydropyrimidine and Oxazolohexahydropyrimidoazepine Scaffolds
B. A. Trofimov
1
,
Olesya A Shemyakina
1
,
Anastasiya G. Mal’kina
1
,
Anton V Stepanov
1
,
Olga G Volostnykh
1
,
Igor Ushakov
1
,
Alexander V. Vashchenko
1
Publication type: Journal Article
Publication date: 2016-11-01
scimago Q2
wos Q2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
The popular organic superbases 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) underwent annulation with electron-deficient propargylic alcohols [EWG = CN, C(O)Ph, CO2Me] to afford functionalized condensed hexahydropyrimidine systems, [1,3]oxazolo[3,2-a]pyrrolo[2,1-b]hexahydropyrimidines and [1,3]oxazolo[3′,2′:3,4] hexahydropyrimido[1,2-a]azepines, in good to high yields. The reactions proceeded regioselectively and, in most cases, stereoselectively under mild conditions (without catalyst, 20–25 °C). The synthesized compounds, owing to their potential rich chemistry, are novel promising precursors for pyrimidine-based pharmaceuticals.
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Total citations:
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Trofimov B. A. et al. Organic Superbases in Annulation with Propargylic Alcohols: Straightforward Synthesis of the Functionalized Oxazolopyrrolohexahydropyrimidine and Oxazolohexahydropyrimidoazepine Scaffolds // European Journal of Organic Chemistry. 2016. Vol. 2016. No. 33. pp. 5465-5469.
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Trofimov B. A., Shemyakina O. A., Mal’kina A. G., Stepanov A. V., Volostnykh O. G., Ushakov I., Vashchenko A. V. Organic Superbases in Annulation with Propargylic Alcohols: Straightforward Synthesis of the Functionalized Oxazolopyrrolohexahydropyrimidine and Oxazolohexahydropyrimidoazepine Scaffolds // European Journal of Organic Chemistry. 2016. Vol. 2016. No. 33. pp. 5465-5469.
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RIS
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TY - JOUR
DO - 10.1002/ejoc.201600977
UR - https://doi.org/10.1002/ejoc.201600977
TI - Organic Superbases in Annulation with Propargylic Alcohols: Straightforward Synthesis of the Functionalized Oxazolopyrrolohexahydropyrimidine and Oxazolohexahydropyrimidoazepine Scaffolds
T2 - European Journal of Organic Chemistry
AU - Trofimov, B. A.
AU - Shemyakina, Olesya A
AU - Mal’kina, Anastasiya G.
AU - Stepanov, Anton V
AU - Volostnykh, Olga G
AU - Ushakov, Igor
AU - Vashchenko, Alexander V.
PY - 2016
DA - 2016/11/01
PB - Wiley
SP - 5465-5469
IS - 33
VL - 2016
SN - 1434-193X
SN - 1099-0690
ER -
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BibTex (up to 50 authors)
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@article{2016_Trofimov,
author = {B. A. Trofimov and Olesya A Shemyakina and Anastasiya G. Mal’kina and Anton V Stepanov and Olga G Volostnykh and Igor Ushakov and Alexander V. Vashchenko},
title = {Organic Superbases in Annulation with Propargylic Alcohols: Straightforward Synthesis of the Functionalized Oxazolopyrrolohexahydropyrimidine and Oxazolohexahydropyrimidoazepine Scaffolds},
journal = {European Journal of Organic Chemistry},
year = {2016},
volume = {2016},
publisher = {Wiley},
month = {nov},
url = {https://doi.org/10.1002/ejoc.201600977},
number = {33},
pages = {5465--5469},
doi = {10.1002/ejoc.201600977}
}
Cite this
MLA
Copy
Trofimov, B. A., et al. “Organic Superbases in Annulation with Propargylic Alcohols: Straightforward Synthesis of the Functionalized Oxazolopyrrolohexahydropyrimidine and Oxazolohexahydropyrimidoazepine Scaffolds.” European Journal of Organic Chemistry, vol. 2016, no. 33, Nov. 2016, pp. 5465-5469. https://doi.org/10.1002/ejoc.201600977.