Synthesis of Isoxazolyl Oxadiazolines and Thiazolidinones.

Abstract

Oxadiazole derivativesOxadiazole derivatives R 0290 Synthesis of Isoxazolyl Oxadiazolines and Thiazolidinones. -Isoxazolyl oxadiazolines (III) and thiazolidinones (V) and (VII) are prepared by cycloaddition reactions of (I) with (II) and (I) or (VI) with (IV) (no yields given). -(RAJANARENDAR*, E.; AFZAL, M.; RAMU, K.; Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 42 (2003) 4, 927-930; Dep. Chem., Kakatiya Univ., Warangal 506 009, India; Eng.) -M. Bohle 32-094

An Overview of the Literature on the Synthetic Routes to Azolyloxadiazoles

“…4‐(5‐Methylisoxazol‐3‐yl)‐3‐phenyl‐5‐aryl‐4,5‐dihydro‐1,2,4‐oxadiazoles 67 have been prepared by benzonitrile oxide 66 addition to 3‐benzalamino‐5‐methylisoxazoles 65 (Scheme ) .…”

Synthesis of 3-(4-(Benzo[d]thiazol-2-yl)phenyl)-5-aryl-1,3,5-oxadiazinane-4-thiones and 1-(4-(Benzo[d]thiazol-2-yl)phenyl)-5-methyl-3-aryl-1,3,5-triazinane-2-thiones

“…9 Threecomponent condensation of N-(3-methyl-5-styryl-4-isoxazolyl)-N-arylureas, paraformaldehyde, and primary amines using montmorillonite K-10 in the absence of solvent under microwave irradiation led to isoxazolyl [1,3,5]triazinan-2-ones in high yields. Condensation of N-(3-methyl 5-stryryl, 4-isoxazolyl) with paraformaldehyde under similar conditions was demonstrated to provide isoxazolyl [1,3,5]oxadiazinan-4-ones in excellent yields by Rajanareder et al 10 1,3,5-Triazinan-2-ones are useful for the protection of amino groups, 11 as well as for the synthesis of polyamines, 12 and poly and functional aminoalcohols. 13 Water-soluble triazinan-2-ones have been used as fertilizers.…”

Three-component solvent-free diastereoselective formation of oxo-thiazolidinylthiazoles under microwave irradiation

“…The 1 H NMR spectra of the products showed distinct doublets at ca δ 1.50 (d, 6H, J = 8 Hz) for C 5"' -CH 3 (2a-e) and distinct doublets at ca δ 2.72 (d, 4H, J = 7 Hz) for C 5"' -CH 2 COOH (2f-j) of thiazolidinone ring, and singlets at ca δ 3.10 for C 2"' -H, so the diastereomers obtained were assigned the trans configuration. [6][7][8] An integrated chemical process has proved to be effective for realising a multi-step one-pot, solvent-free synthesis enabling isolation of an intermediate from the environment through in situ generation followed by consumption. In summary, we have devised a method for one-pot expeditious, diastereoselective synthesis of heteryl analogues of fungitoxic bibenzyls employing microwave technique in solvent-free conditions, which may find application in organic syntheses.…”