A new conjugated addition of trialkyl phosphites and alkylidenephosphoranes to 3-ω-azideoacetyl coumarin synthesis of some 1,2,3,4-triazaphospholes, triazoles, and azido-coumarin derivatives
✍ Scribed by Ashraf A. Sediek; Abeer A. Shaddy; Wafaa M. Abdou
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 2011
- Tongue
- English
- Weight
- 313 KB
- Volume
- 48
- Category
- Article
- ISSN
- 0022-152X
- DOI
- 10.1002/jhet.743
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✦ Synopsis
Abstract
A new and efficient conjugate addition of trimethyl and triethyl phosphites to 3‐ω‐azidoacetylcoumarin (1) has been studied. The reaction proceeded smoothly at r.t. furnishing 1,2,3,4‐triazaphosphole coumarin derivatives 4a, 4b in ∼75% yields. Linear substituted triazoles 10b, 11a were also obtained from the reactions of 1 with α‐keto ylides, acetyl‐ and benzoylmethylene triphenylphosphoranes. Contrary to these results, Wittig reaction was occurred when 1 was allowed to react with α‐alkoxycarbonylmethylene‐ and cyanomethylenetriphenylphosphoranes 7c, 7d, 7e as well as with methylidene‐ and benzylidenetriphenylphosphoranes 8b, 10a resulting in the formation of the corresponding olefins either as an intermediate 14b or as final products 11b, 11c, 12a. J. Heterocyclic Chem., (2011).