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SYNTHESIS OF AROMATIC HETEROCYCLES CONSTRUCTION OF THE RING SKELETON

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.

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SYNTHESIS OF AROMATIC HETEROCYCLES CONSTRUCTION OF THE RING SKELETON

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  1. 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

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

  3. Strategy a) - 6-membered rings

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

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

  6. Cycloaddition with ortho-Quinodimethanes Electrocyclic ring opening

  7. Nitrene Insertion Generation of nitrenes

  8. React. of nitrenes

  9. Nitrene insertion - Heterocyclic synthesis

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