Pyrroline

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Pyrrolines, also known under the name dihydropyrroles, are three different heterocyclic organic chemical compounds that differ in the position of the double bond. Pyrrolines are formally derived from the aromate pyrrolebyhydrogenation. 1-Pyrroline is a cyclic imine, whereas 2-pyrroline and 3-pyrroline are cyclic amines.


1-Pyrroline	2-Pyrroline	3-Pyrroline

Substituted pyrrolines

Notable examples of pyrrolines containing various substituents include:

2-Acetyl-1-pyrroline, an aroma compound with a white bread-like smell
Thienamycin, a beta-lactam antibiotic
MTSL, a chemical used for certain NMR experiments
Pyrrolysine, an unusual proteinogenic amino acid
1-Pyrroline-5-carboxylic acid, a biosynthetic metabolite
Porphyrin, consisting of two alternating pairs of pyrrol and pyrroline connected via methine (=CH-) bridges

N-substituted pyrrolines can be generated by ring-closing metathesis.^[1]

^ Marcelle L. Ferguson, Daniel J. O'leary, And Robert H. Grubbs "Ring-closing Metathesis Synthesis Of N-boc-3-pyrroline" Org. Synth. 2003, volume 80, p. 85. doi:10.15227/orgsyn.080.0085

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