524022-74-0Relevant academic research and scientific papers
Exploratory applications of 2-nitrobenzaldehyde-derived Morita–Baylis–Hillman adducts as synthons in the construction of drug-like scaffolds
Idahosa, Kenudi C.,Davies-Coleman, Michael T.,Kaye, Perry T.
, p. 417 - 430 (2019/01/24)
Morita–Baylis–Hillman adducts, prepared from 2-nitrobenzaldehyde precursors and either methyl acrylate or methyl vinyl ketone, have been used as critical synthons in the preparation of α-[(alkylamino)methyl]cinnamate esters and their but-3-en-2-one analogs, cinnamate ester-azidothymidine (AZT) conjugates, 2-quinolone and quinoline derivatives. Computer docking studies have been conducted to explore the potential of the cinnamate ester–AZT conjugates as potential dual-action HIV-1 integrase–reverse transcriptase (IN–RT) inhibitors. The results further demonstrate the applicability of Morita–Baylis–Hillman methodology in the construction of complex drug-like scaffolds.
Facile synthesis of biarylmethanes and tetrasubstituted arenes: Via a base-mediated [3 + 3] benzannulation reaction of Morita-Baylis-Hillman adducts and unsaturated sulfones
Yadav, Deepak,Sharma, Sunil K.,Menon, Rajeev S.
, p. 4073 - 4076 (2019/04/30)
A facile DBU-mediated [3 + 3] benzannulation reaction of 1,3-bis-sulfonyl propenes and Morita-Baylis-Hillman (MBH) bromides is described. The benzannulation reaction afforded bis-sulfonyl biarylmethanes/arenes with complete regioselectivity. The products
Baylis-Hillman-derived N,N′-disubstituted piperazines: Structural and preliminary computational studies
Idahosa, Kenudi C.,Lee, Yi-Chen,Nyoni, Dubekile,Kaye, Perry T.,Caira, Mino R.
scheme or table, p. 2972 - 2976 (2011/06/21)
Exploratory studies towards the preparation of potential HIV-1 protease and integrase inhibitors have led to the synthesis of Baylis-Hillman-derived N,N′-disubstituted piperazines. X-ray crystallographic, computer modelling and NMR techniques have been us
The Baylis-Hillman approach to quinoline derivatives
Familoni, Oluwole B.,Klaas, Phindile J.,Lobb, Kevin A.,Pakade, Vusumzi E.,Kaye, Perry T.
, p. 3960 - 3965 (2008/09/18)
Baylis-Hillman reactions of 2-nitrobenzaldehydes with various activated alkenes afford adducts that undergo reductive cyclisation to quinoline derivatives. The chemo- and regioselectivity of cyclisation appears to be influenced by the choice of both the substrate and the reagent system, and competing reactions have been observed. The Royal Society of Chemistry 2006.
Synthesis of 3-substituted-4-hydroxyquinoline N-oxides from the Baylis-Hillman adducts of o-nitrobenzaldehydes
Lee, Ka Young,Kim, Jeong Mi,Kim, Jae Nyoung
, p. 385 - 390 (2007/10/03)
The reaction of the Baylis-Hillman adducts 1b-f derived from o-nitrobenzaldehydes in trifluoroacetic acid in the presence of triflic acid (0.2equiv.) afforded 3-substituted-4-hydroxyquinoline N-oxides 2b-e and 2a in good to moderate yields. The reaction mechanism was evidenced by the experiment with 1f, the Baylis-Hillman adduct of 2-nitrobenzaldehyde N-tosylimine, as the one involving N-hydroxyisoxazoline as the key intermediate.
