96308-06-4Relevant academic research and scientific papers
Effective microwave-assisted approach to 1,2,3-triazolobenzo-diazepinones via tandem Ugi reaction/catalyst-free intramolecular azide–alkyne cycloaddition
Mazur, Maryna O.,Zhelavskyi, Oleksii S.,Zviagin, Eugene M.,Shishkina, Svitlana V.,Musatov, Vladimir I.,Kolosov, Maksim A.,Shvets, Elena H.,Andryushchenko, Anna Yu,Chebanov, Valentyn A.
supporting information, p. 678 - 687 (2021/04/09)
A novel catalyst-free synthetic approach to 1,2,3-triazolobenzodiazepinones has been developed and optimized. The Ugi reaction of 2-azidobenzaldehyde, various amines, isocyanides, and acids followed by microwave-assisted intramolecular azide–alkyne cycloaddition (IAAC) gave a series of target heterocyclic compounds in moderate to excellent yields. Surprisingly, the normally required ruthenium-based catalysts were found to not affect the IAAC, only making isolation of the target compounds harder while the microwave-assisted catalyst-free conditions were effective for both terminal and non-terminal alkynes.
A general and efficient approach to 2H-indazoles and 1H-pyrazoles through copper-catalyzed intramolecular N-N bond formation under mild conditions
Hu, Jiantao,Cheng, Yongfeng,Yang, Yiqing,Rao, Yu
supporting information; experimental part, p. 10133 - 10135 (2011/10/09)
A new efficient copper-catalyzed intramolecular amination reaction has been developed to readily synthesise a wide variety of multi-substituted 2H-indazole and 1H-pyrazole derivatives from easily accessible starting materials under mild conditions. A highly selective ligand for estrogen receptor β was prepared in three steps by employing this method. The Royal Society of Chemistry 2011.
Exploiting the acylating nature of the imide-ugi intermediate: A straightforward synthesis of tetrahydro-1,4-benzodiazepin-2-ones
Mossetti, Riccardo,Saggiorato, Desiree,Tron, Gian Cesare
experimental part, p. 10258 - 10262 (2012/02/02)
We describe a simple and novel protocol for the synthesis of tetrahydro-1,4-benzodiazepin-2-ones with three points of diversity, exploiting the acylating properties of the recently rediscovered Ugi-imide. The final compounds can be easily prepared in thre
Cycloaddition reactions of imines with 3-thiosuccinic anhydrides: Synthesis of the tricyclic core of martinellic acid
Ng, Pui Yee,Masse, Craig E.,Shaw, Jared T.
, p. 3999 - 4002 (2007/10/03)
Arylthio-substituted succinic anhydrides undergo cycloaddition reactions with imines to produce γ-lactams in high yield and with high diastereoselectivity. The origin of the selectivity is proposed to result from anion-π repulsion in the transition state. The utility of this technique is demonstrated in a synthesis of the carbon framework common to the alkaloids martinellic acid and martinelline in five steps.
Comparison of the Ease of Thermolysis of Ortho-Substituted Phenyl Azides Having α,β or β,γ Imine Functions
Smith, Peter A. S.,Budde, Gregory F.,Chou, Shang-Shing P.
, p. 2062 - 2066 (2007/10/02)
o-Azidobenzaldehyde benzylimine (7) thermolyzes 34 times faster than phenyl azide and 1.6 times faster than p-chlorobenzaldehyde o-azidoanil (8), whereas benzaldehyde (o-azidobenzyl)imine (9) and acetophenone (o-azidobenzyl)imines (10a-e) show little or no rate enhancement over phenyl azide.An electrocyclic mechanism can account for the rates of 7 and 8 relative to each other but not of 8 relative to phenyl azide; 9 and 10a-e appear to thermolyze by nitrene formation, even though a mechanism through intramolecular cycloaddition may in principle be available.A mechanism based on electrostatic effects in a dipolar transition state can corr elate the effects of different types of α,β-unsaturated ortho substituents.
