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Pyrrolidine is a base. Its basicity is typical of other dialkyl amines. [7] Relative to many secondary amines, pyrrolidine is distinctive because of its compactness, a consequence of its cyclic structure. Pyrrolidine is used as a building block in the synthesis of more complex organic compounds.
The Boger pyridine synthesis is a cycloaddition approach to the formation of pyridines named after its inventor Dale L. Boger, who first reported it in 1981. [1] The reaction is a form of inverse-electron demand Diels-Alder reaction in which an enamine reacts with a 1,2,4- triazine to form the pyridine nucleus.
Among the most important representatives of the pyrrolidine alkaloids are hygrin and cuscohygrin. [2] Another representative is the (-)- codonopsinine . [ 3 ] Furthermore, ruspolinone , norruspolinone and norruspoline also belong to this alkaloid group.
A reaction of an azomethine ylide with an alkene is shown above, and results in a pyrrolidine. [12] This kind of reactions can be used to synthesis Ullazine. [13] While dipolarophiles are typically α,β-unsaturated carbonyl compounds, there have been many recent advances in developing new types of dipolarophiles. [14]
The Enders SAMP/RAMP hydrazone alkylation begins with the synthesis of the hydrazone from a N,N-dialkylhydrazine and a ketone or aldehyde [14]. The hydrazone is then deprotonated on the α-carbon position by a strong base, such as lithium diisopropylamide (LDA), leading to the formation of a resonance stabilized anion - an azaenolate.
In 2008 P.S. Baran et al. [48] reported a new method for the synthesis of 1,3-diols using a variant of the Hofmann–Löffler–Freytag reaction. In 2017, Nagib et al. [49] [50] reported a new method for the synthesis of 1,2-amino-alcohols using a variant of the Hofmann–Löffler–Freytag reaction to promote β selective C-H amination of ...
There are multiple ways to synthesize PAs and their derivatives. A flexible strategy would be to start with a Boc (tert-Butoxycarbonyl) protected pyrrole molecule and use specific reaction for synthesis into the desired compound. [19] A general strategy for the production of pyrrolizidine alkaloids is described, starting from intermediate (+)−9.
The next year, Emil Fischer isolated proline from casein and the decomposition products of γ-phthalimido-propylmalonic ester, [5] and published the synthesis of proline from phthalimide propylmalonic ester. [6] The name proline comes from pyrrolidine, one of its constituents. [7]