16765-79-0Relevant articles and documents
Synthesis of β-carbolines via a silver-mediated oxidation of tetrahydro-β-carbolines
Durham, Sierra D.,Sierra, Brianna,Gomez, Maximillian J.,Tran, Jennifer K.,Anderson, Marc O.,Whittington-Davis, Nick A.,Eagon, Scott
, p. 2747 - 2750 (2017)
The oxidation of tetrahydro-β-carbolines to β-carbolines using silver carbonate was developed as an alternative to current methods. The oxidation is extremely mild and provides the products in modest to good yields after purification. A number of functional groups are tolerated by this methodology, including reduction-sensitive groups which are often cleaved with other methods. Though the mechanism is not fully understood, the reaction proceeds in an open flask, is not sensitive to light or moisture, and provides a viable synthetic route to compounds that are not easily prepared via other methodologies.
Facile synthesis of isoquinolines, β-carbolines, and 3-deazapurines
Huang, Wenhua,Li, Jingyi,Ou, Lihua
, p. 2137 - 2143 (2007)
Isoquinoline, β-carbolines, and 3-deazapurines were prepared in 52-81% yields via oxidative decarboxylation of cyclic α-amino acids using ammonium persulfate as an oxidant in the presence of catalytic silver. Copyright Taylor & Francis Group, LLC.
A convenient synthesis of β-carbolines by iron-catalyzed aerobic decarboxylative/dehydrogenative aromatization of tetrahydro-β-carbolines under air
Mohamad Arshad, Ahmad Saifuddin,Meesala, Ramu,Hanapi, Nur Aziah,Mordi, Mohd Nizam
, (2021/02/12)
A convenient synthesis for the conversion of various substituted tetrahydro-β-carbolines has been developed by iron-catalyzed decarboxylative/dehydrogenative aromatization to construct aromatic β-carbolines under air atmosphere. In the presence of a FeCl3 catalyst, this reaction exhibited a good functional group tolerance to produce corresponding β-carbolines in good yields in the absence of any additive. Additionally, the utility of the method was highlighted in the gram-scale synthesis of important natural β-carboline synthons norharmane (2a) and harmane (2b), which the latter provide practical access towards eudistomin N and nostocarboline.
Bifunctional thiosquaramide catalyzed asymmetric reduction of dihydro-β-carbolines and enantioselective synthesis of (-)-coerulescine and (-)-horsfiline by oxidative rearrangement
Nachtigall, Fabiane M.,Santos, Leonardo S.,Sathish, Manda
, p. 38672 - 38677 (2020/11/05)
Tetrahydro-β-carboline (THBC) is a tricyclic ring system that can be found in a large number of bioactive alkaloids. Herein, we report a simple and efficient method for the synthesis of enantiopure THBCs through a chiral thiosquaramide (11b) catalyzed imine reduction of dihydro-β-carbolines (17a-f). The in situ generated Pd-H employed as hydride source in the reaction of differently substituted chiral THBCs (18a-f) afforded high selectivities (R isomers, up to 96% ee) and good isolated yields (up to 88%). Moreover, the chiral thiosquaramide used also afforded exceptional catalyst activity in the syntheses of (-)-coerulescine (5) and (-)-horsfiline (6) with excellent enantioselectivities up to 98% and 93% ee, respectively, via an enantioselective oxidative rearrangement approach.
