By Alan R. Katritzky (Eds.)
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Additional info for Aminomethylenemalonates and Their Use in Heterocyclic Synthesis
27 71 using Mukaiyama’s reagent. These somewhat unstable carbodiimides were not isolated but were treated directly with (C2H5)3N to afford the desired 4-cyanooxazoles 98 in excellent yield. 5. 5. 7 Entry R1 R1 R2HN O 95 R1 98 R2 Yield (%)b Product CN 1 H N t-C4H9 t-C4H9HN 88 O CN 2 CH3 N i-C3H7 i-C3H7HN 81 CH3 O CN 3 i-C3H7 N i-C3H7 i-C3H7HN 74 O i-C3H7 CN 4 i-C3H7 N t-C4H9 t-C4H9HN a b Data from ref. 70. Yield is the conversion of the carbodiimide to the oxazole. 77 O i-C3H7 Synthesis of Oxazoles 23 Prager and co-workers72–74 used the photochemical rearrangement of 2-acylisoxazol-5-ones to prepare 2,4-disubstituted, 2,5-disubstituted, and 2,4,5-trisubstituted oxazoles 15.
36 Fukushima and Ibata83 reported direct evidence for the formation of an acyl nitrile ylide intermediate during Rh2(OAc)4-catalyzed reactions of a-diazoacetophenones 133 with nitriles in the presence of dimethylacetylene dicarboxylate (DMAD). 37). They proposed that 137 arose from the acyl nitrile ylide 136 via 1,5-cyclization, whereas 1,3-diploar-cycloaddition of 136 with DMAD followed by a 1,5-hydrogen shift produced 138. The authors showed that 138 did not arise via a Diels-Alder reaction of 137 with DMAD.
52). Mechanistically, the authors proposed initial formation of a di(a-arylalkanoyl)Hg(II) species 192 from reaction of the enol tautomer of propiophenone with mercury(II) tosylate. Reaction of 192 with benzonitrile generates 193, which collapses to the oxirane 194 with loss of mercury. 52 toluenesulfonic acid then affords 2,4-diphenyl-5-methyloxazole 196. 14. 4. Cyclization of an amide or urea with an a-haloketone is a well-established and still widely used method to prepare oxazoles. 14. 16 Entry R1 O R2 191 R2 Product Yield (%) C6H5 1 C6H5 N H C6H5 51 O C6H4-4-Cl 2 4-Cl-C6H4 N H C6H5 50 O C6H4-4-Cl 3 4-Cl-C6H4 N CH2CH3 C6H5 O 71 C2H5 COOC2H5 4 COOC2H5 N H C6H5 a 47 O Data from ref.
Aminomethylenemalonates and Their Use in Heterocyclic Synthesis by Alan R. Katritzky (Eds.)