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2004
Amino acids
U 0400
Synthesis of Fused Heteroarylprolines and Pyrrolopyrroles. — The synthesis of
hetarylprolines is achieved on two different ways. First approach involves the
46- 185 fused
allylation of oxoproline derivative (I) followed by Wacker oxidation to give a dione
(IV) which can cyclize with hydrazine or benzylamine to pyridazinoproline (V) or pyrrolopyrrole derivatives (VII)/(VIII), respectively. In the latter case, the product structure can be controlled by the reaction conditions. The second approach involves the
aldol condensation of oxoproline (I) with α-amino aldehydes (IX) followed by
acid-catalyzed cyclization. Various selective manipulations at nitrogen and at the carboxyl group are demonstrated. — (JEANNOTTE, G.; LUBELL*, W. D.; J. Org.
Chem. 69 (2004) 14, 4656-4662; Dep. Chem., Univ. Montreal, Montreal,
Que. H3C 3J7, Can.; Eng.) — Mischke
2004
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