142114-84-9Relevant academic research and scientific papers
Catalytic Staudinger/aza-Wittig sequence by in situ phosphane oxide reduction
Van Kalkeren, Henri A.,Te Grotenhuis, Colet,Haasjes, Frank S.,Hommersom,Rutjes, Floris P. J. T.,Van Delft, Floris L.
supporting information, p. 7059 - 7066 (2013/11/06)
A Staudinger/aza-Wittig reaction sequence is described that is catalytic in phosphorus. Towards this end, the phosphane oxide is reduced in situ by diphenylsilane, which allows for substoichiometric amounts of the catalyst 5-phenyldibenzophosphole to be used. The substrate scope is investigated and benzoxazoles, benzodiazepine imidates and a 2-methoxypyrrole were successfully synthesized. These investigations show that a fast aza-Wittig reaction is required to obtain high yields. A catalytic Staudinger/aza-Wittig reaction sequence, involving in situ phosphane oxide reduction, was successfully developed. Benzoxazoles, benzodiazepine imidates and 2-methoxypyrrole were synthesized without phosphane oxide waste products. Copyright
Efficient solid-phase synthesis of highly functionalized 1,4-benzodiazepin-5-one derivatives and related compounds by intramolecular aza-wittig reactions
Gil, Carmen,Braese, Stefan
, p. 2680 - 2688 (2007/10/03)
Due to their widespread biological activities and favorable pharmacokinetic properties, benzodiazepines were among the first classes of small molecules to be synthesized on solid supports. Since then, there have been numerous reports on the synthesis of similar skeletons. We have employed the T1 triazene linker to yield 1,4-benzodiazepin-5-one. Starting from various substituted triazene resins, cleavage in the presence of an azide donor, such as trimethylsilylazide, gave rise to aryl azides. Intramolecular aza-Wittig reactions produced the appropriately functionalized N-heterocycles. By using this route, the natural product deoxyvasicinone and related compounds were prepared.
Facile Synthesis of 1,4-Benzodiazepin-5-one Derivatives via Intramolecular Aza-Wittig Reaction. Application to an Efficient Synthesis of O-Benzyl DC-81
Eguchi, Shoji,Yamashita, Keizo,Matsushita, Yuji,Kakehi, Akikazu
, p. 4006 - 4012 (2007/10/02)
The tandem Staudinger/aza-Wittig reaction of N-(o-azidobenzoyl)-α-amino acid esters gave the corresponding 1,4-benzodiazepin-5-one derivatives in moderate to good yields.This method was applied successfully to a new efficient synthesis of BzlDC-81.
