RING-TRANSFORMATIONS OF PYRIMIDINES BY INTRAMOLECULAR DIELS-ALDER REACTIONS. SYNTHESIS OF ANNELATED PYRIDINES

DOI: 10.1016/0040-4020(89)80111-5

Source and publish data:

Tetrahedron p. 803 - 812 (1989)

Update date:2022-08-05

Topics:

Authors:

Frissen, A. E.

Marcelis, A. T. M.

Plas, H. C. van der

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Article abstract of DOI:10.1016/0040-4020(89)80111-5

Pyrimidines carrying an ω-alkyne side-chain -XCH2CH2CCH (X=O,N,S,SO,SO2) at the 2 or 5 position undergo intramolecular inverse electron demand Diels-Alder reactions across the C-2 and C-5 positions; elimination of hydrogen (or alkyl) cyanide from the intermediate adducts leads to condensed pyridines.The influence of the hetero atom (X) in the dienophilic side-chain and that of substituents in the pyrimidine ring on the reactivity is discussed.

Full text of DOI:10.1016/0040-4020(89)80111-5

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