ADDITIONAL CYCLE FORMATION FROM 2-DIALKOXYPHOSPHONYLMETHYLTHIAZOLE

Abstract

Diisopropoxyphosphonyl-2-(4-methylthiazolyl)methane I reacts with carhonyl and α-halo-carbonyl compounds by three routes. In the case of Knoevenagel or Horner-Wadsworth-Emmons reactions the corresponding ethylenes were produced, whereas employing α-halo-carbonyls as partners resulted in pyrrolo[2.1b]thiazoles. 1-Phosphonyl-1-(2-thiazolyl)- ethylene undergoes smoothly [4+2] and [3+2] cycloaddition reactions.

Key Words:

• Dialkoxyphosphonyl-2-(4-methylthiazolyl)methanes
• 1-phosphonyl-1-thiazolylethylenes
• 6-dialkoxyphosphonylpyrrolo[2.1b]thiazoles
• 3-methoxycarbonyl-5-dialkoxyphosphonyl-5-(4-methylthizol-2-yl)-2-pyrazoline
• 5-dialkoxyphosphonyl-5-(4-methylthiazol-2-yl)-bicyclo[2.2.1]hept-2-ene