88229-16-7Relevant articles and documents
Diamine Synthesis via the Nitrogen-Directed Azidation of σ- And π-C-C Bonds
Nguyen, Tin V. T.,Wang, Ming-Ming,Waser, Jerome
supporting information, p. 11969 - 11975 (2021/08/24)
Diamines are essential building blocks for the synthesis of agrochemicals, drugs, and organic materials, yet their synthesis remains challenging, as both nitrogens need to be differentiated and diverse substitution patterns (1,2, 1,3, or 1,4) are required. We report herein a new strategy giving access to 1,2, 1,3, and 1,4 amido azides as orthogonally protected diamines based on the nitrogen-directed diazidation of alkenes, cyclopropanes, and cyclobutanes. Commercially available copper thiophene-2-carboxylate (CuTc, 2 mol %) as catalyst promoted the diazidation of both πand σ C-C bonds within 10 min in the presence of readily available oxidants and trimethylsilyl azide. Selective substitution of the formed α-amino azide by carbon nucleophiles (electron-rich aromatic, malonate, organosilicon, organoboron, organozinc, and organomagnesium compounds) was then achieved in a one-pot fashion, leading to the formation of 1,2-, 1,3-, and 1,4-diamines with the amino groups protected orthogonally as an amide/carbamate and an azide.
Synthesis of thiochromans via [3+3] annulation of aminocyclopropanes with thiophenols
Wang, Ming-Ming,Jeon, Seongmin,Waser, Jer?me
supporting information, p. 9123 - 9127 (2020/11/30)
We report the one-pot synthesis of 4-amino thiochromans using simple aminocyclopropanes and thiophenols through a formal [3+3] annulation reaction. This reaction proceeds under mild conditions with good functional group tolerance. The thiochroman core was
N-(R-cyclopropyl)fluorobenzimidoyl phosphonates
Onys'ko,Klyukovskii,Bezdudnyi
, p. 418 - 423 (2015/04/14)
Reaction of N-(R-cyclopropyl)benzimidoyl chloride with triethyl phosphite has yielded the corresponding N-(R-cyclopropyl)-substituted benzimidoyl phosphonates existing predominantly in the E-configuration [E: Z ≈ (8-10): 1] at room temperature. 19/s