71960-57-1Relevant academic research and scientific papers
Design and Synthesis of Highly Potent HIV-1 Protease Inhibitors Containing Tricyclic Fused Ring Systems as Novel P2 Ligands: Structure-Activity Studies, Biological and X-ray Structural Analysis
Ghosh, Arun K.,Nyalapatla, R.Prasanth,Kovela, Satish,Rao, Kalapala Venkateswara,Brindisi, Margherita,Osswald, Heather L.,Amano, Masayuki,Aoki, Manabu,Agniswamy, Johnson,Wang, Yuan-Fang,Weber, Irene T.,Mitsuya, Hiroaki
, p. 4561 - 4577 (2018/05/31)
The design, synthesis, and biological evaluation of a new class of HIV-1 protease inhibitors containing stereochemically defined fused tricyclic polyethers as the P2 ligands and a variety of sulfonamide derivatives as the P2′ ligands are described. A numb
Reductive free-radical alkylations and cyclisations mediated by 1-alkylcyclohexa-2,5-diene-1-carboxylic acids
Baguley, Paul A.,Walton, John C.
, p. 2073 - 2082 (2007/10/03)
A range of 1-alkylcyclohexa-2,5-diene-1-carboxylic acids were prepared by Birch reduction-alkylation of benzoic acid and their efficiency as mediators of alkyl radical chain addition and cyclisation processes was investigated. Reductive alkylations were respectably successful, even with only one or two equivalents of alkene, for secondary, tertiary and benzylic radicals. Reaction of 1-[2-(cyclohex-2-enyloxy)ethyl]cyclohexa-2,5-diene-1-carboxylic acid yielded the product of exo-trig-cyclisation, i.e. 7-oxabicyclo[4.3.0]nonane, in a yield comparable to that obtained from the tributyltin hydride induced cyclisation of 3-(2′-iodoethoxy)-cyclohexene. This, together with the isolation of both exo- and endo-cyclisation products from 1-[2-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-ylmethoxy)ethyl]cyclohexa-2,5-diene- 1-carboxylic acid established that ring closures could also be satisfactorily mediated with these reagents. Preparations were completely free of metal contaminants and direct reduction of the alkyl radicals, prior to addition or cyclisation, was completely absent. However, the desired products were accompanied by alkylbenzenes, together with by-products from the initiator decompositions, and this complicated work-up. Failure to obtain 1-[2-(prop-2-yn-1-yloxy)cyclohexyl]cyclohexa-2,5-diene-1-carboxylic acid in Birch reductive alkylations with trans-1-iodo-2-(prop-2-yn-1-yloxy)cyclohexane (and the corresponding bromide) indicated a limitation on precursor synthesis. The Birch reduction-alkylation was not of universal applicability and was suppressed for alkyl halides having β-substituents.
Allenyl Allylic Ethers: Synthesis and Thermal Rearrangements
Dulcere, Jean-Pierre,Crandall, Jack,Faure, Robert,Santelli, Maurice,Agati, Valerie,Mihoubi, Mohamed N.
, p. 5702 - 5708 (2007/10/02)
Application of the sequence halogenation/dehydrohalogenation/isomerization to alkenes 1a-g affords allenyl allylic ethers 5a-g.Thermal isomerizations of 5a,d,e proceed by Claisen rearrangement, while 5b,c,f,g are transformed by alternate modes of c
A New Synthetic Route to β-Bromoprop-2-ynyl Mixed Acetals and Bromovinyl Bis-allyl Mixed Acetals, Precursors of α-Methylene-γ-Butyrolactones
Dulcere, J. P.,Mihoubi, M. N.,Rodriguez, J.
, p. 237 - 239 (2007/10/02)
Cohalogenation by N-bromosuccinimide in methanol of β-bromoallenyl ethers (3a-g) or allyl allenyl ethers (8d-f) affords unsaturated halogeno-compounds (5a-g) or (9d-f) which are converted via homolytic carbocyclization into α-methylene-γ-butyrolactones (7a-g).
A Radical Cyclisation Route to α-Methylene-γ-butyrolactones
Srikrishna, Adusumilli
, p. 587 - 588 (2007/10/02)
A three-step synthesis of α-methylene-β-butyrolactones is described, via radical cyclisation of 2-bromoalkyl prop-2-ynyl ethers (5) to 3-methylenetetrahydrofurans (6) using a tin catalyst.
