56069-64-8Relevant academic research and scientific papers
A facile synthesis of [E]-α-cyanocinnamic aldehydes from Baylis-Hillman adducts
Ravichandran
, p. 2185 - 2188 (2001)
A facile synthesis of stereochemically pure [E]-α-cyanocinnamic aldehydes from Baylis-Hillman adducts is described.
Catalytic Enantioselective Hetero-[6+4] and-[6+2] Cycloadditions for the Construction of Condensed Polycyclic Pyrroles, Imidazoles, and Pyrazoles
Bertuzzi, Giulio,Th?gersen, Mathias Kirk,Giardinetti, Maxime,Vidal-Albalat, Andreu,Simon, Adam,Houk,J?rgensen, Karl Anker
supporting information, p. 3288 - 3297 (2019/03/05)
The development of the first chemo-, regio-, and stereoselective hetero-[6+4] and-[6+2] cycloadditions of heteroaromatic compounds via amino aza-and diazafulvenes is presented. Pyrroles, imidazoles, and pyrazoles substituted with a formyl group react with an aminocatalyst to generate an electron-rich hetero-6?€-component that reacts in a chemo-, regio-, and stereoselective manner with electron-deficient dienes and olefins. For the hetero-[6+4] cycloaddition of the pyrrole system with dienes, a wide variation of both reaction partners is possible, providing attractive pyrrolo-azepine products in high yields and excellent enantioselectivities (99% ee). The hetero-[6+4] cycloaddition reaction concept is extended to include imidazoles and pyrazoles, giving imidazolo-and pyrazolo-azepines. The same activation concept is successfully employed to include hetero-[6+2] cycloadditions of the pyrrole system with nitroolefins, giving important pyrrolizidine-alkaloid scaffolds. Experimental NMR and mechanistic studies allowed for the identification of two different types of intermediates in the reaction. The first intermediate is the result of a rapid formation of an iminium ion, which generates a hetero-6?€ aminofulvene intermediate as a mixture of two isomers. Density functional theory calculations were used to determine the mechanism and sources of asymmetric induction in the hetero-[6+4] and-[6+2] cycloadditions. After formation of the reactive hetero-6?€-components, a stepwise addition occurs with the diene or olefin, leading to a zwitterionic intermediate that undergoes cyclization to afford the cycloadduct, followed by eliminative catalyst release. The stereoselectivity is controlled by the second step, and computations elaborate on the various substrate and catalyst effects that alter the experimentally observed enantioselectivities. The computational studies provided a basis for improving the enantioselectivity of the hetero-[6+2] cycloaddition.
An efficient catalyst-free one-pot synthesis of primary amides from the aldehydes of the Baylis-Hillman reaction
Narendar Reddy, Thatikonda,Raktani, Bikshapathi,Perla, Ramesh,Ravinder, Mettu,Vaidya, Jayathirtha Rao,Babu, N. Jagadeesh
, p. 9203 - 9209 (2017/08/29)
Herein, a facile and efficient method for the preparation of allyl amides from the aldehyde of Baylis-Hillman adducts has been developed using a hydroxylamine/methanol system under a catalyst-free condition. The effects of solvents and temperature on the reaction and substituents on the phenyl ring have been examined. This method is best demonstrated by its advantages such as operational simplicity, moderate to excellent yields, short reaction time, and simple reaction procedure. Most importantly, the reaction proceeds smoothly in the absence of a catalyst and an external oxidant.
Design, synthesis, and biological evaluation of 4-H pyran derivatives as antimicrobial and anticancer agents
Reddy, Thatikonda Narendar,Ravinder, Mettu,Bikshapathi, Raktani,Sujitha, Pombala,Kumar, C. Ganesh,Rao, Vaidya Jayathirtha
, p. 2832 - 2844 (2017/10/06)
A series of pyran derivatives (5–27) were synthesized in good yields by utilizing Baylis–Hillman chemistry and were further investigated for their in vitro anticancer, antibacterial, and antifungal activities. Most of the tested compounds exhibited promis
Hypervalent iodine catalysis for selective oxidation of Baylis-Hillman adducts via in situ generation of o-iodoxybenzoic acid (IBX) from 2-iodosobenzoic acid (IBA) in the presence of oxone
Bikshapathi, Raktani,Prathima, Parvathaneni Sai,Rao, Vaidya Jayathirtha
supporting information, p. 10300 - 10304 (2016/12/07)
An efficient, environmentally benign, eco-friendly protocol for selective oxidation of primary and secondary Baylis-Hillman alcohols to the corresponding carbonyl compounds has been developed. We have demonstrated the catalytic use of o-iodoxybenzoic acid
Substituted Bicyclic Pyrimidine Compounds with Tubulin and Multiple Receptor Inhibition
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Paragraph 0047, (2015/10/28)
This invention provides substituted bicyclic pyrimidine compounds and pharmaceutically acceptable salts, hydrates, and solvates of the compounds, each having tubulin and multiple receptor inhibition properties. Methods of treating a patient diagnosed with
Chemoselective palladium-catalyzed cyanation of alkenyl halides
Powell, Kimberley J.,Han, Li-Chen,Sharma, Pallavi,Moses, John E.
supporting information, p. 2158 - 2161 (2014/05/06)
A palladium-catalyzed cyanation of alkenyl halides using acetone cyanohydrin is described. A number of structurally diverse alkenylic nitrile containing compounds was prepared in one step under optimized conditions. The reaction proved to be efficient, chemoselective, easy to perform, and tolerant of a number of functional groups.
IBX-mediated dehydrogenation of substituted β-oxonitriles
Klahn, Philipp,Kirsch, Stefan F.
, p. 3149 - 3155 (2014/06/09)
A convenient method for the mild dehydrogenation of β-oxonitriles is presented. When treated with o-iodoxybenzoic acid (IBX), a range of these compounds were transformed into their unsaturated counterparts. Furthermore, we show that the products of the dehydrogenation can react in situ, undergoing rapid hetero-Diels-Alder reactions with enol ethers to give multiply substituted dihydropyrans. We also describe the dehydrogenation of cyclic β-oxonitriles, which leads to the formation of substituted phenols. Copyright
Synthesis and biological evaluation of new epalrestat analogues as aldose reductase inhibitors (ARIs)
Reddy, Thatikonda Narendar,Ravinder, Mettu,Bagul, Pankaj,Ravikanti, Keerthi,Bagul, Chandrakant,Nanubolu, Jagadeesh Babu,Srinivas, Kolupula,Banerjee, Sanjay K.,Rao, Vaidya Jayathirtha
, p. 53 - 66 (2014/01/06)
Baylis-Hillman chemistry derived four series of new epalrestat analogues were synthesized. Three structural changes are introduced in these 39 new epalrestat analogues synthesized. All compounds were evaluated for their in vitro aldose reductase inhibitor
Structure-activity relationship study of first selective inhibitor of excitatory amino acid transporter subtype 1: 2-Amino-4-(4-methoxyphenyl)-7- (naphthalen-1-yl)-5-oxo-5,6,7,8-tetrahydro-4 H -chromene-3-carbonitrile (UCPH-101)
Erichsen, Mette N.,Huynh, Tri H. V.,Abrahamsen, Bjarke,Bastlund, Jesper F.,Bundgaard, Christoffer,Monrad, Olja,Bekker-Jensen, Anders,Nielsen, Christina W.,Frydenvang, Karla,Jensen, Anders A.,Bunch, Lennart
experimental part, p. 7180 - 7191 (2010/12/25)
The excitatory amino acid transporters (EAATs) are expressed throughout the central nervous system, where they are responsible for the reuptake of the excitatory neurotransmitter (S)-glutamate (Glu).(1)Recently, we have reported the discovery of the first subtype selective EAAT1 inhibitor 2-amino-4-(4-methoxyphenyl)-7-(naphthalen-1-yl)-5-oxo-5,6,7,8-tetrahydro-4H- chromene-3-carbonitrile (UCPH-101) (1b) and presented an introductory structure-activity relationship (SAR) study.(2)Here, we present a detailed SAR by the design, synthesis, and pharmacological evaluation of analogues 1g-1t. By comparison of potencies of 1b, 1h, and 1i versus 1j, it is evident that potency is largely influenced by the chemical nature of the R1 substituent. The study also demonstrates that any chemical change of the functional groups or a change to the parental scaffold results in the complete loss of inhibitory activity of the compounds at EAAT1. Finally, a bioavailability study of UCPH-101 determined the half-life to be 30 min in serum (rats) but also that it was not able to penetrate the blood-brain barrier to any significant degree.
