117838-48-9Relevant academic research and scientific papers
Rhodium-Catalyzed N-tert-Butoxycarbonyl (Boc) Amination by Directed C H Bond Activation
Wippich, Julian,Truchan, Nadina,Bach, Thorsten
supporting information, p. 2083 - 2087 (2016/07/16)
N-tert-Butoxycarbonyl azide (BocN3) was shown to be an efficient and economic source for the directed introduction of N-Boc protected amino groups into the thiophene and benzene nucleus. Yields for the amination of 2-pyridin-2-ylthiophenes (10 examples) were 52–88%. For the amination of the respective benzenes (10 examples) yields between 54% and 99% were recorded with an improved reactivity observed for substrates that bear an electron-withdrawing group. The reaction was applied to short total syntheses of the indoloquinoline alkaloids quindoline and cryptolepine. The facile removal of the Boc protecting group was the key to the success of the syntheses. The scope of the reaction was extended to a C(sp3) H bond amination and to the amination of 2-phenyloxazoline. For the amination of 2-pyridin-2-ylbenzene a kinetic deuterium isotope effect of 2.0 was determined. (Figure presented.) .
An alternative synthesis of quindoline and one of its closely related derivatives
Csanyi,Timari,Hajos
, p. 3959 - 3969 (2007/10/03)
The alkaloid Quindoline (13) and one of its tetracyclic isomer indazolo[2,3-a]quinoline (8) have been synthesised utilising the Pd(0)- catalysed cross-coupling reaction of pivaloylamino phenylboronic acid (2) with substituted quinolines.
Synthesis of Indazoloquinolines
Reddy, Y. Padma,Reddy, K. Kondal
, p. 563 - 564 (2007/10/02)
A number of 2-(o-nitrophenyl)quinolines (Ia-e) have been synthesised and converted via amines (IIa-e) into corresponding azides (IIIa-e).Thermolysis and deoxygenation of 2-(o-azidophenyl)-(IIIa-e) and 2-(o-nitrophenyl)-(Ia-e)-quinolines respectively lead
