THE REACTION OF 2,4-BIS(4-METHOXYPHENYL)-l,3,2,4-D1THIA DIPHOSPHETANE-2,4-DISULFIDE (LR) WITH COUMARIN OXIME AND HYDRAZONE DERIVATIVES. SYNTHESIS OF BENZOPYRANO (3,2-D)-Δ⁵-2,1,3-OXAZA- AND 1,2,3-DIAZA-PHOSPHOLINES

Abstract

2,4-Bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide (Lawesson's reagent, LR, 1) reacted with coumarin oxime (2) and its 6-methyl derivative (3) to give compounds 6 and 7, respectively. Oxidation of 6 and 7 with KMnO₄ afforded the corresponding oxo- derivatives, 8 and 9. Benzopyrano(3,2-d)-Δ⁵-1,2,3-diazaphospholine-3-sulfide derivatives (14 and 15) were obtained through the reaction of LR with coumarin hydrazones (10 and 11), respectively. Mannich reaction using morpholine and/or benzylamine on compounds 14 and 15 afforded the Mannich bases 16–19. Alkylation of 14 and 15 with ethyl iodide produced compounds 20 and 21.

Key Words:

• 2
• 4-Bis(4-methoxyphenyl)-1
• 3
• 2
• 4-dithiadiphosphetane-2
• 4-disulfide (LR) coumarin oxime
• coumarin hydrazone
• biological properties