7139-42-6Relevant articles and documents
Chiral exploration of 6,12-diphenyldibenzo[b,f][1,5]diazocine with stable conformation
Li, Zheng-Yi,Pan, Yong,Jin, Lin-Lin,Yin, Yue,Yang, Bao-Zhu,Sun, Xiao-Qiang
, p. 134 - 139 (2017)
A first optical resolution of 6,12-diphenyldibenzo[b,f][1,5]diazocine with stable boat conformation was achieved by chiral supercritical fluid chromatography (SFC). The absolute configurations of enantiomers were first assigned and determined by X-ray cry
Indium-Catalyzed Annulation of o-Acylanilines with Alkoxyheteroarenes: Synthesis of Heteroaryl[b]quinolines and Subsequent Transformation to Cryptolepine Derivatives
Yonekura, Kyohei,Shinoda, Mika,Yonekura, Yuko,Tsuchimoto, Teruhisa
, (2018/04/17)
We disclose herein the first synthetic method that is capable of offering heteroaryl[b]quinolines (HA[b]Qs) with structural diversity, which include tricyclic and tetracyclic structures with (benzo)thienyl, (benzo)furanyl, and indolyl rings. The target HA[b]Q is addressed by the annulation of o-acylanilines and MeO-heteroarenes with the aid of an indium Lewis acid that effectively works to make two different types of the N-C and C-C bonds in one batch. A series of indolo[3, 2-b]quinolines prepared here can be subsequently transformed to structurally unprecedented cryptolepine derivatives. Mechanistic studies showed that the N-C bond formation is followed by the C-C bond formation. The indium-catalyzed annulation reaction thus starts with the nucleophilic attack of the NH2 group of o-acylanilines to the MeO-connected carbon atom of the heteroaryl ring in an SNAr fashion, and thereby the N-C bond is formed. The resulting intermediate then cyclizes to make the C-C bond through the nucleophilic attack of the heteroaryl-ring-based carbon atom to the carbonyl carbon atom, providing the HA[b]Q after aromatizing dehydration.
Palladium(ii)-catalysed regioselective synthesis of 3,4-disubstituted quinolines and 2,3,5-trisubstituted pyrroles from alkenes via anti-Markovnikov selectivity
Senadi, Gopal Chandru,Hu, Wan-Ping,Garkhedkar, Amol Milind,Boominathan, Siva Senthil Kumar,Wang, Jeh-Jeng
supporting information, p. 13795 - 13798 (2015/09/07)
A novel strategy has been identified for the regioselective synthesis of 3,4-disubstituted quinolines and 2,3,5-trisubstituted pyrroles from simple alkenes via anti-Markovnikov selectivity under palladium catalysis. The salient features are synthesis of two different heterocycles, readily available starting materials, broad substrate scope, moderate to good yields and use of molecular oxygen as a terminal oxidant.