- First example of electrophile induced Baylis-Hillman reaction: A novel facile one-pot synthesis of indolizine derivatives
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Treatment of pyridine-2-carboxaldehyde with activated alkenes such as alkyl vinyl ketones and cyclic enones in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) provides a novel facile one-pot synthesis of indolizine derivatives, thus for the first time describing an electrophile induced Baylis-Hillman reaction.
- Basavaiah, Deevi,Rao, Anumolu Jaganmohan
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- Selective hydrogenation of indolizines: An expeditious approach to derive tetrahydroindolizines and indolizidines from Morita-Baylis-Hillman adducts
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In this study, we describe the hydrogenation of indolizines derived from Morita-Baylis-Hillman adducts. We demonstrate that functionalized tetrahydroindolizines and indolizidines can be prepared selectively, at low pressure, by simply adjusting the acidity of the medium. Using this simple and straightforward strategy, substituted tetrahydroindolizines and indolizidines were obtained diastereoselectively in high yield.
- Teodoro, Bruno V. M.,Correia, José Tiago M.,Coelho, Fernando
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p. 2529 - 2538
(2015/03/18)
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- Indolizines 3. The synthesis of 2-vinylindolizines and their reaction with dienophiles
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The Wittig olefination of 2-acetylindolizine 2 by methylenetriphenylphosphorane gives 2-isopropenylindolizine 3 with a 99 percent yield; its reaction with dimethyl acetylenedicarboxylate, maleic anhydride, benzoquinone, dimethyl maleate, dimethyl fumarate, N-ethylmaleimide and 4-methyl-1,2,4-triazoline-3,5-dione gives mainly Michael adducts to the available 3 position of the indolizine, and only low amounts of cyclo-addition products.Reaction of 2 with methoxymethylenetriphenylphosphorane gives 54percent of 2-(α-methyl-β-methoxy)vinylindolizine 4; this very electronrich diene undergoes extensive decomposition with most dienophiles; only dimethyl maleate and N-ethylmaleimide gave identifiable products, Michael adducts and cyclo-adducts, and with low yields.
- Siberdt, F.,Nasielski, J.
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- Indolizine Studies. Part 2. Synthesis and NMR Spectroscopic Analysis of 2-Substituted Indolizines
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Thermal cyclisation of 3-acetoxy-3-(2-pyridyl)-2-methylenepropionate esters and related compounds provides convenient access to 2-substituted indolizines.Detailed one- and two-dimensional NMR spectroscopic analysis of the title compounds has facilitated interpretation of their 1H and 13C NMR spectra.
- Bode, Moira L.,Kaye, Perry T.
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p. 1809 - 1814
(2007/10/02)
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