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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
Author(s) -
Sediek Ashraf A.,
Shaddy Abeer A.,
Abdou Wafaa M.
Publication year - 2011
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.743
Subject(s) - chemistry , coumarin , conjugated system , wittig reaction , conjugate , medicinal chemistry , organic chemistry , stereochemistry , mathematical analysis , mathematics , polymer
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).