Caenogastropoda during Mesozoic times by Bandel K.

By Bandel K.

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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. 102. simplicity of the reaction makes this an efficient method for parallel synthesis or in combinatorial reactions, despite the widely varying yields. Several examples that illustrate this method are discussed in this section. Meguro and co-workers37 used this method, among others, to prepare a variety of potential antidiabetic agents.

CH3OOC 2. 39). This oxazole ester was a useful starting material for a variety of analogs screened as agrochemicals. Moody and co-workers80,85–94 extensively investigated and refined rhodiumcatalyzed additions of diazocarbonyl compounds to construct oxazoles. Severalsignificant developments from these studies are described in the following schemes. 40). 7. 7. 9 Entry 145 O OC2H5 146 R Product Yield (%) SO2C6H5 N C2H5 1 C2H5 52 OC2H5 O SO2C6H5 2 N 2-Cl-C6H4 2-Cl-C6H4 56 OC2H5 O SO2C6H5 3 N 3-CH3O-C6H4 3-CH3O-C6H4 24 O OC2H5 SO2C6H5 4 N C6H5 C 6H 5 a Data from ref.

17). 17 Electophilic iodination using I2 has also been employed to effect net oxidation of oxazolines to 2-substituted 4-oxazolecarboxylic acid esters. 18). Here, the oxazoline 57 was first treated with LiHMDS and TMSCl to protect the carbamate as a silyl amide followed by treatment with KHMDS and iodine to generate the oxazole 58. Interestingly, the authors60 also isolated diastereomeric spirocyclic ortho ester aminals 59 in 25 to 30% yield under these reaction conditions. Synthesis of Oxazoles 15 CH3 CH3 CH3 CH3 N BocHN 1.

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