Journal ArticleDOI
Enaminones: versatile intermediates for natural product synthesis*
Joseph P. Michael,C. B. De Koning,David Gravestock,Gladys D. Hosken,Arthur S. Howard,C. M. Jungmann,Rui W. M. Krause,Andrew S. Parsons,Stephen C. Pelly,Trevor V. Stanbury +9 more
Reads0
Chats0
TLDR
In this article, an overview of the chemistry of enaminones and related compounds containing the structural unit N-CaC-Z (Za COR, CO2R, CN, NO2, S O 2Ar, etc.).Abstract:
Efforts in our laboratories to devise a general approach to the synthesis of alkaloids focus on the versatile reactivity of enaminones and related compounds containing the structural unit N-CaC-Z (Za COR, CO2R, CN, NO2 ,S O 2Ar, etc.). This lecture presents an overview of our research with these useful building blocks. Themes to be elaborated include chemo- selectivity and diastereoselectivity in reactions of enaminones, and the challenge of controlling absolute stereochemistry.read more
Citations
More filters
Journal ArticleDOI
One-Pot Synthesis, X-ray Single Crystal and Molecular Insight of Enaminone-Based β-Morpholino-/N-Methylpiperazinyl-/Pyrrolidinylpropiophenone
Assem Barakat,Saied M. Soliman,Matti Haukka,Abdullah Mohammed Al-Majid,Mohammad Shariful Islam,M. Ali,Mohammed Rafi Shaik +6 more
TL;DR: One-pot synthesis of enaminones, (E)-1-(4-chlorophenyl)-3-morpholinoprop-2-en-1-one 1,(E)- 1-(4chloroacetophenone)-3-(4methylpiperazin-1yl)prop-2.1-en 1-one-one 2, and (E) 1-( 4-chloroprop]-3-(pyrrolidin)-1-yl)-prop- 2.5-4 h at 102 °C yielded the requisite enamin
Journal ArticleDOI
Hydrogen-bonding patterns in enaminones: (2Z)-1-(4-bromophenyl)-2-(pyrrolidin-2-ylidene)ethanone and its piperidin-2-ylidene and azepan-2-ylidene analogues.
TL;DR: The title compounds are characterized by bifurcated intra- and intermolecular hydrogen bonding between the secondary amine and carbonyl groups, which establishes a six-membered hydrogen-bonded ring.
Journal ArticleDOI
Methyl (2E)-2-cyano-3-(dimethyl-amino)-prop-2-enoate.
TL;DR: In the title compound, C7H10N2O2, the dimethylamino group is twisted slightly relative to the acrylate fragment, forming a dihedral angle of 11.6 (1)°.
Journal ArticleDOI
(Z)-3-[1-(4-Methoxy-anilino)ethyl-idene]-4,5-dihydro-furan-2(3H)-one.
TL;DR: The dihydro-furan-one ring of C13H15NO3 is planar to within 0.012 ǫ(4)ÕA and it forms a dihedral angle of 42.8 Ô(2)° with the benzene ring.
Journal ArticleDOI
(Z)-Ethyl 3-(2,6-diisopropyl-anilino)but-2-enoate.
Manuel Amézquita-Valencia,Simón Hernández-Ortega,Gloria Alejandra Suárez-Ortiz,Armando Cabrera +3 more
TL;DR: The title compound, C18H27NO2, crystallizes as the enamine form with Z geometry, where the β-enaminoester fragment forms a dihedral angle of 87.5 (1)° with the isopropylphenyl frame.
References
More filters
BookDOI
Alkaloids : chemical and biological perspectives
TL;DR: In this paper, the total synthesis of amaryllidaceae alkaloids has been studied using radical cyclization reactions in total syntheses of naturally occurring indole alkaloid.
Book
Strategies and Tactics in Organic Synthesis
TL;DR: This paper presents the first total Synthesis of several Natural Products Based On Alkyne-Co2(Co2)6 Complexes, and discusses the design and synthesis of Cooperative "Pinwheel" Fluorescent Sensors, and the application of Silicon-Ass Intramolecular Cross-Coupling.