Open Access
2-Amino-4,5-dihydrothiophene-3-carbonitriles: A New Synthesis, Quantum Chemical Studies, and Mannich-Type Reactions Leading to New Hexahydrothieno[2,3-d]pyrimidines
Viktor V Dotsenko
1, 2, 3
,
Alexander V Bespalov
1
,
Arthur Vashurin
3
,
Inna V. Aksenova
2
,
E A Chigorina
4, 5
,
Publication type: Journal Article
Publication date: 2021-11-19
scimago Q1
wos Q2
SJR: 0.773
CiteScore: 7.1
Impact factor: 4.3
ISSN: 24701343
PubMed ID:
34901606
General Chemistry
General Chemical Engineering
Abstract
trans-2-Amino-4-aryl-5-benzoyl-4,5-dihydrothiophene-3-carbonitriles were prepared either by the reaction of 3-aryl-2-cyanothioacrylamides with α-thiocyanatoacetophenone or by the Michael-type addition of cyanothioacetamide to α-bromochalcones followed by intramolecular cyclization. The mechanism of the first reaction was studied using high-level quantum chemical calculations. Density functional theory (DFT) studies were carried out to determine the mechanism of the first reaction. A new approach toward the construction of the thieno[2,3-d]pyrimidine core system was demonstrated by the reaction of the prepared dihydrothiophenes with HCHO and RNH2 under noncatalyzed Mannich conditions.
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12
Total citations:
12
Citations from 2024:
9
(75%)
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GOST
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Dotsenko V. V. et al. 2-Amino-4,5-dihydrothiophene-3-carbonitriles: A New Synthesis, Quantum Chemical Studies, and Mannich-Type Reactions Leading to New Hexahydrothieno[2,3-d]pyrimidines // ACS Omega. 2021. Vol. 6. No. 48. pp. 32571-32588.
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Dotsenko V. V., Bespalov A. V., Vashurin A., Aksenov N. A., Aksenova I. V., Chigorina E. A., Krivokolysko S. G. 2-Amino-4,5-dihydrothiophene-3-carbonitriles: A New Synthesis, Quantum Chemical Studies, and Mannich-Type Reactions Leading to New Hexahydrothieno[2,3-d]pyrimidines // ACS Omega. 2021. Vol. 6. No. 48. pp. 32571-32588.
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RIS
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TY - JOUR
DO - 10.1021/acsomega.1c04141
UR - https://doi.org/10.1021/acsomega.1c04141
TI - 2-Amino-4,5-dihydrothiophene-3-carbonitriles: A New Synthesis, Quantum Chemical Studies, and Mannich-Type Reactions Leading to New Hexahydrothieno[2,3-d]pyrimidines
T2 - ACS Omega
AU - Dotsenko, Viktor V
AU - Bespalov, Alexander V
AU - Vashurin, Arthur
AU - Aksenov, Nicolai A.
AU - Aksenova, Inna V.
AU - Chigorina, E A
AU - Krivokolysko, Sergey G.
PY - 2021
DA - 2021/11/19
PB - American Chemical Society (ACS)
SP - 32571-32588
IS - 48
VL - 6
PMID - 34901606
SN - 2470-1343
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2021_Dotsenko,
author = {Viktor V Dotsenko and Alexander V Bespalov and Arthur Vashurin and Nicolai A. Aksenov and Inna V. Aksenova and E A Chigorina and Sergey G. Krivokolysko},
title = {2-Amino-4,5-dihydrothiophene-3-carbonitriles: A New Synthesis, Quantum Chemical Studies, and Mannich-Type Reactions Leading to New Hexahydrothieno[2,3-d]pyrimidines},
journal = {ACS Omega},
year = {2021},
volume = {6},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021/acsomega.1c04141},
number = {48},
pages = {32571--32588},
doi = {10.1021/acsomega.1c04141}
}
Cite this
MLA
Copy
Dotsenko, Viktor V., et al. “2-Amino-4,5-dihydrothiophene-3-carbonitriles: A New Synthesis, Quantum Chemical Studies, and Mannich-Type Reactions Leading to New Hexahydrothieno[2,3-d]pyrimidines.” ACS Omega, vol. 6, no. 48, Nov. 2021, pp. 32571-32588. https://doi.org/10.1021/acsomega.1c04141.
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