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Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes

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2018
asia.201800645.pdf (1.748Mb)
Authors
Aleksić, Jovana
Stojanović, Milovan
Baranac-Stojanović, Marija
Article (Accepted Version)
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Abstract
We present an efficient, simple, metal- and solvent-free silica-gel-promoted synthesis of functionalized conjugated dienes by sequential aza-Michael/Michael reactions by starting from commercially available primary amines and propiolic esters. The scope and usefulness of the method is demonstrated for 31examples, including a range of propiolic esters, aliphatic amines, and differently substituted aromatic amines. For aliphatic amines, the products were obtained within 0.5 to 4h in 52 to 85% yield, compared with 3.5 to 22h under classical solution-phase synthesis, which proceeds with similar or lower yields. The method was found to be particularly useful for weakly nucleophilic aromatic amines, which provided products in 21 to 73% yield over 2.5 to 9.5h compared with yields of 0 to 49% over 1 to 6d under standard solution-phase conditions, and for more hydrophobic esters that gave products in yields of 47 to 79% over 1 to 3h compared with 0 to 45% over 4 to 114h in solvent.
Keywords:
amines / conjugation / green chemistry / Michael addition / propiolic esters
Source:
Chemistry-An Asian Journal, 2018, 13, 14, 1811-1835
Publisher:
  • Wiley-V C H Verlag Gmbh, Weinheim
Projects:
  • Experimental and theoretical study of reactivity and biological activity of stereodefined thiazolidines and their synthetic analogues (RS-172020)
  • Reinforcement of the Faculty of Chemistry, University of Belgrade, towards becoming a Center of Excellence in the region of WB for Molecular Biotechnology and Food research (EU-256716)
Note:
  • This is the peer-reviewed version of the following article: Aleksić, J.; Stojanović, M.; Baranac-Stojanović, M. Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes. Chemistry - An Asian Journal 2018, 13 (14), 1811–1835. https://doi.org/10.1002/asia.201800645
  • http://cer.ihtm.bg.ac.rs/handle/123456789/2451

DOI: 10.1002/asia.201800645

ISSN: 1861-4728

PubMed: 29757499

WoS: 000439497300008

Scopus: 2-s2.0-85050126437
[ Google Scholar ]
4
3
URI
http://cer.ihtm.bg.ac.rs/handle/123456789/3135
Collections
  • Radovi istraživača / Researchers' publications
Institution
IHTM
TY  - JOUR
AU  - Aleksić, Jovana
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2018
UR  - http://cer.ihtm.bg.ac.rs/handle/123456789/3135
AB  - We present an efficient, simple, metal- and solvent-free silica-gel-promoted synthesis of functionalized conjugated dienes by sequential aza-Michael/Michael reactions by starting from commercially available primary amines and propiolic esters. The scope and usefulness of the method is demonstrated for 31examples, including a range of propiolic esters, aliphatic amines, and differently substituted aromatic amines. For aliphatic amines, the products were obtained within 0.5 to 4h in 52 to 85% yield, compared with 3.5 to 22h under classical solution-phase synthesis, which proceeds with similar or lower yields. The method was found to be particularly useful for weakly nucleophilic aromatic amines, which provided products in 21 to 73% yield over 2.5 to 9.5h compared with yields of 0 to 49% over 1 to 6d under standard solution-phase conditions, and for more hydrophobic esters that gave products in yields of 47 to 79% over 1 to 3h compared with 0 to 45% over 4 to 114h in solvent.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Chemistry-An Asian Journal
T1  - Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes
VL  - 13
IS  - 14
SP  - 1811
EP  - 1835
DO  - 10.1002/asia.201800645
ER  - 
@article{
author = "Aleksić, Jovana and Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2018",
url = "http://cer.ihtm.bg.ac.rs/handle/123456789/3135",
abstract = "We present an efficient, simple, metal- and solvent-free silica-gel-promoted synthesis of functionalized conjugated dienes by sequential aza-Michael/Michael reactions by starting from commercially available primary amines and propiolic esters. The scope and usefulness of the method is demonstrated for 31examples, including a range of propiolic esters, aliphatic amines, and differently substituted aromatic amines. For aliphatic amines, the products were obtained within 0.5 to 4h in 52 to 85% yield, compared with 3.5 to 22h under classical solution-phase synthesis, which proceeds with similar or lower yields. The method was found to be particularly useful for weakly nucleophilic aromatic amines, which provided products in 21 to 73% yield over 2.5 to 9.5h compared with yields of 0 to 49% over 1 to 6d under standard solution-phase conditions, and for more hydrophobic esters that gave products in yields of 47 to 79% over 1 to 3h compared with 0 to 45% over 4 to 114h in solvent.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Chemistry-An Asian Journal",
title = "Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes",
volume = "13",
number = "14",
pages = "1811-1835",
doi = "10.1002/asia.201800645"
}
Aleksić J, Stojanović M, Baranac-Stojanović M. Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes. Chemistry-An Asian Journal. 2018;13(14):1811-1835
Aleksić, J., Stojanović, M.,& Baranac-Stojanović, M. (2018). Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes.
Chemistry-An Asian JournalWiley-V C H Verlag Gmbh, Weinheim., 13(14), 1811-1835.
https://doi.org/10.1002/asia.201800645
Aleksić Jovana, Stojanović Milovan, Baranac-Stojanović Marija, "Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes" 13, no. 14 (2018):1811-1835,
https://doi.org/10.1002/asia.201800645 .

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