Programmed Sequential Additions to Halogenated Mucononitriles
Publication type: Journal Article
Publication date: 2020-10-06
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
33021798
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
Dihalomucononitriles were synthesized and their reactivity evaluated to assess their ability to function as linchpin reagents. Bis(2-chloroacrylonitrile) and bis(2-bromoacrylonitrile) were synthesized from 2,1,3-benzothiadiazole and undergo conjugate addition/elimination reactions with both nitrogen (40-95% yield) and carbon nucleophiles (72-93% yield). Secondary amines undergo monosubstitutions, while carbon nucleophiles are added twice. The sequence of addition of the nucleophiles could be controlled to give mixed addition products. The multicomponent coupling products could then be converted to natural product like motifs using intramolecular cyclization reactions.
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Metrics
13
Total citations:
13
Citations from 2025:
3
(23.08%)
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GOST
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Zahara A. J. et al. Programmed Sequential Additions to Halogenated Mucononitriles // Organic Letters. 2020. Vol. 22. No. 20. pp. 8065-8069.
GOST all authors (up to 50)
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Zahara A. J., Hinds E. M., Nguyen A. L., Wilkerson Hill S. M. Programmed Sequential Additions to Halogenated Mucononitriles // Organic Letters. 2020. Vol. 22. No. 20. pp. 8065-8069.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.orglett.0c03007
UR - https://doi.org/10.1021/acs.orglett.0c03007
TI - Programmed Sequential Additions to Halogenated Mucononitriles
T2 - Organic Letters
AU - Zahara, Adam J
AU - Hinds, Elsa M
AU - Nguyen, Andrew L.
AU - Wilkerson Hill, Sidney M
PY - 2020
DA - 2020/10/06
PB - American Chemical Society (ACS)
SP - 8065-8069
IS - 20
VL - 22
PMID - 33021798
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2020_Zahara,
author = {Adam J Zahara and Elsa M Hinds and Andrew L. Nguyen and Sidney M Wilkerson Hill},
title = {Programmed Sequential Additions to Halogenated Mucononitriles},
journal = {Organic Letters},
year = {2020},
volume = {22},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/acs.orglett.0c03007},
number = {20},
pages = {8065--8069},
doi = {10.1021/acs.orglett.0c03007}
}
Cite this
MLA
Copy
Zahara, Adam J., et al. “Programmed Sequential Additions to Halogenated Mucononitriles.” Organic Letters, vol. 22, no. 20, Oct. 2020, pp. 8065-8069. https://doi.org/10.1021/acs.orglett.0c03007.