No abstract

Three-component coupling of aldehydes, vinylcyclopropyl carbinols, and nitriles in the presence of 10 mol% TMSOTf at -40 to 0 °C in dichloromethane affords a novel class of (3-oxabicyclo[4.2.0]octanyl)amides in high yields with excellent selectivity, whereas (1-vinylcyclobutyl)methanol provides the corresponding (1-(5-aryltetrahydrofuran-3-yl)cyclobutyl)amides under similar conditions. This is the first report on the synthesis of oxabicycles through a sequential Prins/Wagner/Ritter process.

A new series of 2-(3-oxo-3-phenylpropanoyl)-3-(substituted aryl)-1-thiazolidin-4-ones has been synthesized by cyclocondensation of ketoanils (the condensation products of 2, 4-dioxo-4phenyl butanal with primary amines) with mercaptoacetic acid. The chemical structures of the synthesized compounds were elucidated by elemental analysis, molecular weight determination, and UV, IR, 1 H, 13 C and DEPT-135 NMR spectral measurements. Bactericidal and fungicidal activates of the new products were studied in virto against Staphylococcus aureus and Eseherichia coli bacteria and Asparigillus niger and Rhizoctia bataticola fungi by using ampicillin and bavistin reference drugs, respectively.

Tandem Prins/Wagner/Ritter Process for the Stereoselective Synthesis of (3-Oxabicyclo[4.2.0]octanyl)amide and (1-(5-Aryltetrahydrofuran-3-yl)cyclobutyl)amide Derivatives. -Three-component reaction of vinylcyclopropyl carbinol (I), aldehydes, and nitriles provides access to the novel oxabicyclooctanyl amides [cf. (IV), (VII)], whilst (1-vinylcyclobutyl)methanol (VII) gives cyclobutyltetrahydrofuran derivatives (IX) under similar conditions. Surprisingly, three-component reaction of carbinol (I) with MeCN and cinnamaldehyde furnishes alcohol (XI) instead of an expected amide. -(SUBBA REDDY*, B. V.; MURALIKRISHNA, K.; YADAV, J. S.; BABU, N. J.; SIRISHA, K.; SARMA, A. V. S.; Org. Biomol. Chem. 13 (2015) 19, 5532-5536, http://dx.doi.org/10.1039/C5OB00031A ; Nat. Prod. Chem., Indian Inst. Chem. Technol., Hyderabad 500 007, India; Eng.) -H. Toeppel 37-162