Azetidine and Indole alkaloid

Azetidine is a saturated heterocyclic organic compound containing three carbon atoms and one nitrogen atom.It is liquid at room temperature, has a strong ammonia odor, and is strongly basic compared with most secondary amines.

Synthesis and generation

Azetidines can be prepared by reducing azetidinones (β-lactams) with lithium aluminum hydride.Even more effective is a mixture of lithium aluminum hydride and aluminum trichloride,which is the source of “AlClH2” and “AlCl2H”.Azetidines can also be produced from 3-amino-1-propanol by a multistep route.Regioselective and diastereoselective syntheses of 2-arylazetidines can be performed from appropriately substituted oxiranes by ring inversions.It is governed by Baldwin’s rules with significant functional group tolerance.Azetidine and its derivatives are relatively rare structural motifs in natural products.They are constituents of mugineic acids and penaresidins. Perhaps the most abundant azetidine-containing natural product is azetidine-2-carboxylic acid, a toxic mimic of proline.

Indole alkaloid

Indole alkaloids are a class of alkaloids that contain an indole moiety; many indole alkaloids also include a prenyl group and are therefore called terpene indole or secologanin tryptamine alkaloids.It contains more than 4100 known different compounds, making it one of the largest classes of alkaloids.Many of them have significant physiological activities, and some of them are used in medicine. The amino acid tryptophan is a biochemical precursor of indole alkaloids.

Category

Indole alkaloids are differentiated on the basis of their biosynthesis.The two types of indole alkaloids are isoprenoids and non-isoprenoids.The latter include terpenoid structural elements, which are synthesized by organisms from dimethylallyl pyrophosphate (DMAPP) and/or isopentenyl pyrophosphate (IPP):

Non-isoprenoid:

• Simple derivatives of indole

• Simple derivatives of β-carbolines

• Pyrroloindole alkaloids

• Indole-3-carbinol

• Indole-3-acetic acid

• Tryptamine

• Carbazoles

Isoprenoids:

• Semiterpenes: Ergot alkaloids

• Monoterpenoids.

• Sidine

• Vinca

• Yohimbe

• Periwinkle

• Strychnine

• Ellipticine

There are also pure structural classifications based on the presence of carbazole, β-carboline, or other units in the carbon skeleton of the alkaloid molecule.About 200 dimerindole alkaloids are known to have two indole groups.