International audienc

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Ammonia may be used in Ugi-type reactions, providing good yields of Ugi-Smiles and Ugi-Mumm adducts under microwave irradiation.

Multicomponent reactions O 0359Thiols in Ugi-and Passerini-Smiles-Type Couplings. -In continuation of a previously published study on the Ugi-Smiles type coupling of benzoxazoles [e.g. (XXV)] and benzothiazoles respectively, a set of more than 40 different combinations of aromatic thiols, carbonyl compounds, amines and isocyanides is investigated in this reaction. In most cases the multicomponent reaction is followed by the Smiles rearrangement leading to thioamides. Lack of that rearrangement furnishes thioimidates in some cases [e.g. (XXVIII)]. A preliminary study of a thio-Passerini-Smiles like coupling reveals that this reaction is strongly restricted to a few reactants [e.g. (XXIX)]. -(BARTHELON, A.; EL KAIM*, L.; GIZOLME, M.; GRIMAUD, L.; Eur. J. Org. Chem. 2008, 35, 5974-5987; Ec. Natl. Super. Tech. Av., F-75015 Paris, Fr.; Eng.) -Nuesgen 16-051

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