142114-82-7Relevant 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.
One pot conversion of azido arenes to N-arylacetamides and N-arylformamides: Synthesis of 1,4-benzodiazepine-2,5-diones and fused [2,1-b]quinazolinones
Kamal, Ahmed,Ramana, A. Venkata,Reddy, K. Srinivasa,Ramana, K. Venkata,Hari Babu,Prasad, B. Rajendra
, p. 8187 - 8190 (2007/10/03)
Sodium iodide in acidic media has been employed for the synthesis of N-arylformamides and N-arylacetamides. The NaI/acetic acid reagent system has also been extended for the synthesis of 1,4-benzodiazepine-2,5-diones, pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones, and fused [2,1-b]quinazolinones.
Synthesis of DNA-interactive pyrrolo[2,1-c][1,4]benzodiazepines by employing polymer-supported reagents: Preparation of DC-81
Kamal, Ahmed,Reddy, K. Laxma,Devaiah,Shankaraiah
, p. 2533 - 2536 (2007/10/03)
Polymer-supported reagents have been utilized for the generation of combinatorial library of substituted pyrrolo[2,1-c][1,4]benzodiazepine derivatives that provides a clean and efficient preparation and does not require conventional purification techniques like chromatography. This methodology involves intra molecular aza-Wittig reaction and has been extended for the synthesis of the natural product DC-81 in good overall yields.
Synthesis of pyrrolo[2,1-c][1,4]benzodiazepine antibiotics via azido reductive cyclization with HMDST
Kamal, Ahmed,Reddy, B.S. Praveen,Reddy, B.S. Narayan
, p. 6803 - 6806 (2007/10/03)
A new facile synthesis of pyrrolo[2,1-c][1,4]benzodiazepine (PBD) ring system has been achieved by reductive cyclization of the azide employing hexamethyldisilathiane (HMDST). The parent unsubstituted PBD and the natural product DC-81 have also been prepared in good overall yields.
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.
Synthesis of pyrrolo[2,1-c][1,4]benzodiazepines via an intramolecular aza-Wittig reaction. Synthesis of the antibiotic DC-81
Molina, Pedro,Diaz, Isidora,Tarraga, Alberto
, p. 5617 - 5630 (2007/10/02)
A new and efficient synthesis of the pyrrolo[2,1-c][1,4]benzodiazepine ring system has been carried out using, as a key step, an intramolecular aza-Wittig reaction of the appropriately substituted N-(2-azidobenzoyl)pyrrolidine-2-carboxaldehydes. The paren
