SYNTHESIS OF AROMATIC HETEROCYCLES CONSTRUCTION OF THE RING SKELETON

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Presentation transcript:

SYNTHESIS OF AROMATIC HETEROCYCLES CONSTRUCTION OF THE RING SKELETON Carbonyl condensation type reactions Cycloadditions with 1,3-dipoles with ortho-quinodimethanes (DA type react.) Nitrene insertion Carbonyl condensations

Strategy a) - 5-membered rings Pyrrole (Paal-Knorr Synthesis s 255) Furan Thiophene

Strategy a) - 6-membered rings

Strategy b 5-membered rings 6-membered rings Enol (or phenol) Enamin (or anilin)

1,3-Dipolar Cycloaddition Only 5-membered rings Alkene / alkyne Ex. ozonolysis

Cycloaddition with ortho-Quinodimethanes Electrocyclic ring opening

Nitrene Insertion Generation of nitrenes

React. of nitrenes

Nitrene insertion - Heterocyclic synthesis

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