Stereospecific Synthesis of 1,4,5,6-Tetrahydropyrimidines via Domino Ring-Opening Cyclization of Activated Aziridines with α-Acidic Isocyanides
Publication type: Journal Article
Publication date: 2018-05-08
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
29738257
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
An expeditious synthetic route to access structurally diverse 1,4,5,6-tetrahydropyrimidines via domino ring-opening cyclization of activated aziridines with α-acidic isocyanides has been established. The transformation proceeds via Lewis acid mediated SN2-type ring opening of activated aziridines with α-carbanion of the isocyanides followed by a concomitant 6- endo- dig cyclization in a domino fashion to furnish the 1,4,5,6-tetrahydropyrimidine derivatives in excellent yields (up to 84%) and also in diastereo- and enantiomerically pure form (dr >99:1, ee >99%).
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Total citations:
43
Citations from 2024:
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(13.96%)
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GOST
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Bhattacharyya A. et al. Stereospecific Synthesis of 1,4,5,6-Tetrahydropyrimidines via Domino Ring-Opening Cyclization of Activated Aziridines with α-Acidic Isocyanides // Organic Letters. 2018. Vol. 20. No. 10. pp. 2925-2928.
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Bhattacharyya A., Kumar Shahi C., Pradhan S., Ghorai M. K. Stereospecific Synthesis of 1,4,5,6-Tetrahydropyrimidines via Domino Ring-Opening Cyclization of Activated Aziridines with α-Acidic Isocyanides // Organic Letters. 2018. Vol. 20. No. 10. pp. 2925-2928.
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RIS
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TY - JOUR
DO - 10.1021/acs.orglett.8b00986
UR - https://doi.org/10.1021/acs.orglett.8b00986
TI - Stereospecific Synthesis of 1,4,5,6-Tetrahydropyrimidines via Domino Ring-Opening Cyclization of Activated Aziridines with α-Acidic Isocyanides
T2 - Organic Letters
AU - Bhattacharyya, Aditya
AU - Kumar Shahi, Chandan
AU - Pradhan, Sajan
AU - Ghorai, Manas K.
PY - 2018
DA - 2018/05/08
PB - American Chemical Society (ACS)
SP - 2925-2928
IS - 10
VL - 20
PMID - 29738257
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
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@article{2018_Bhattacharyya,
author = {Aditya Bhattacharyya and Chandan Kumar Shahi and Sajan Pradhan and Manas K. Ghorai},
title = {Stereospecific Synthesis of 1,4,5,6-Tetrahydropyrimidines via Domino Ring-Opening Cyclization of Activated Aziridines with α-Acidic Isocyanides},
journal = {Organic Letters},
year = {2018},
volume = {20},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/acs.orglett.8b00986},
number = {10},
pages = {2925--2928},
doi = {10.1021/acs.orglett.8b00986}
}
Cite this
MLA
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Bhattacharyya, Aditya, et al. “Stereospecific Synthesis of 1,4,5,6-Tetrahydropyrimidines via Domino Ring-Opening Cyclization of Activated Aziridines with α-Acidic Isocyanides.” Organic Letters, vol. 20, no. 10, May. 2018, pp. 2925-2928. https://doi.org/10.1021/acs.orglett.8b00986.