57675-09-9Relevant articles and documents
Exploiting Alkylquinone Tautomerization for the Total Synthesis of Calothrixin A and B
Mori-Quiroz, Luis M.,Dekarske, Madeline M.,Prinkki, Austin B.,Clift, Michael D.
, p. 12257 - 12266 (2017)
The pentacyclic alkaloid calothrixin B (1) has been synthesized in 5 steps from murrayaquinone A (9). The key step involved the union of boryl aniline 31 with brominated murrayaquinone A (26). In this transformation, alkylquinone 26 undergoes tautomerization to a quinone methide, which is intercepted by boryl aniline 31 to forge a new C-N bond. An intramolecular Suzuki coupling, followed by dehydrogenative aromatization, completed the synthesis of calothrixin B. Subsequent N-oxidation of calothrixin B delivered calothrixin A. The successful synthesis of these alkaloids and the challenges that led to the development of the final synthesis plan are reported herein.
On-water reactivity and regioselectivity of quinones in C-N coupling with amines: Experimental and theoretical study
Martinez-Cifuentes, Maximiliano,Clavijo-Allancan, Graciela,Di Vaggio-Conejeros, Carolina,Weiss-Lopez, Boris,Araya-Maturana, Ramiro
, p. 217 - 224 (2014/03/21)
A study about the oxidative coupling of some representative carbo-and heterocyclic non-symmetrical quinones with aryl-and alkylamines, was carried out comparing dichloromethane and water as reaction mediums. We found that the on-water reactions gave better or, at worst, the same results as a conventional organic medium like dichloromethane. Descriptors derived from conceptual density functional theory and approaches of electrostatic nature, such as the molecular electrostatic potential, were used to explain the observed chemical reactivity and regioselectivity. Further, the on-water conditions were used to obtain 24 new aminoquinones with potential biological activity.
Green protocol for conjugate addition of amines to p-quinones accelerated by water
Yadav, Jhillu S.,Reddy, Basi V. Subba,Swamy, Tallapally,Shankar, Kattela Shiva
experimental part, p. 1317 - 1320 (2009/12/04)
Amines undergo smooth conjugate addition to p-quinones in H2O at ambient temperature in the absence of a catalyst to produce 2-aminoquinones in excellent yields. Significant rate acceleration of this reaction is observed in H2O compa
