41859-54-5Relevant articles and documents
AMINE-BORANES AS BIFUNCTIONAL REAGENTS FOR DIRECT AMIDATION OF CARBOXYLIC ACIDS
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Paragraph 0008-0009; 0063-0064, (2022/03/04)
The present invention generally relates to a process for selective and direct activation and subsequent amidation of aliphatic and aromatic carboxylic acids to afford an amide R3CONR1R2. That the process is capable of delivering gaseous or low-boiling point amines provides a major advantage over existing methodologies, which involves an intermediate of triacyloxyborane-amine complex [(R3CO2)3—B—NHR1R2]. This procedure readily produces primary, secondary, and tertiary amides, and is compatible with the chirality of the acid and amine involved. The preparation of known pharmaceutical molecules and intermediates has also been demonstrated.
Spirooxazoline Synthesis by an Oxidative Dearomatizing Cyclization
Tariq, M. Umair,Moran, Wesley J.
, p. 5153 - 5160 (2020/07/30)
Spirocyclic compounds are of increasing importance owing to their potential applications in the development of new pharmaceuticals. Herein, we describe a new, rapid access to rarely seen spirooxazolines utilizing an I(I)/I(III) reaction manifold. The scope of the cyclization using phenols and naphthols is described along with the stereoselective functionalization of the spirocycles. The application of this method to the formation of dihydrooxazines is also demonstrated.
N-acylcarbazole as a selective transamidation reagent
Kang, Bubwoong,Kuse, Masaki,Okamura, Hironori,Sakai, Asumi,Satoh, Tetsuya,Shinada, Tetsuro,Yasuno, Yoko
, p. 993 - 999 (2020/09/22)
N-acylation reaction offers an opportunity to develop an efficient synthesis of amide group-containing molecules. We found that N-acyl carbazoles showed remarkable selectivity in transamidation. Sterically less hindered primary amines are selectively acylated with N-acyl carbazoles without any additives. Various functional groups such as alcohol, phenol, indole, and aniline moieties are tolerated under mild conditions. The synthetic utility was displayed in one-pot synthesis of an N-acyl polyamine natural product. The terminal amines of spermidine were selectively benzoylated with N-benzoyl carbazole, followed by acetylation reaction accomplished the total synthesis in a highly efficient manner.
