37993-76-3Relevant articles and documents
Palladium-catalyzed domino Heck/intermolecular cross-coupling: efficient synthesis of 4-alkylated isoquinoline derivatives
Yao, Tuanli,Liu, Tao,Zhang, Changhui
, p. 2386 - 2389 (2017)
A highly efficient Pd-catalyzed Heck-type cascade process with 2-(1-alkynyl)benzaldimines has been developed, which provides access to a broad range of 4-alkylated isoquinoline derivatives in moderate to good yields. The σ-alkylpalladium(ii) intermediate in the Heck reaction activates alkynes toward intramolecular nucleophilic attack. This is the first example of a σ-alkylpalladium(ii) intermediate promoting the cyclization of alkynes containing a proximate nucleophilic center.
Reaction of Benzocyclobutenoxides with Nitriles: Synthesis of Hypecumine and Other 3-Substituted Isoquinolines
Fitzgerald, John J.,Michael, Forrest E.,Olofson, R. A.
, p. 9191 - 9194 (1994)
Treatment of benzocyclobuten-2-ols with MeLi affords o-tolualdehyde anions which in the presence of nitriles cyclize to 3-substituted isoquinolines.Examples include the synthesis of the alkaloid hypecumine from the precursors, 14 and 19 (1:1), in 50percen
Cobalt-Mediated Decarboxylative/Desilylative C?H Activation/Annulation Reaction: An Efficient Approach to Natural Alkaloids and New Structural Analogues
Chen, Kang,Lv, Shan,Lai, Ruizhi,Yang, Zhongzhen,Hai, Li,Nie, Ruifang,Wu, Yong
, (2022/02/03)
A Co(II)-mediated decarboxylative/desilylative C?H activation/annulation reaction for the efficient synthesis of 3-arylisoquinolines has been developed. Using alkynyl carboxylic acid and alkynyl silane as terminal alkyne precursors, providing straightforw
Silver/Rhodium Relay Catalysis Enables C?H Functionalization of In Situ Generated Isoquinolines with Sulfoxonium Ylides: Construction of Hexahydrodibenzo[a,g]quinolizine Scaffolds
Li, Quanzhe,Liu, Ruixing,Wei, Yin,Shi, Min
, p. 2664 - 2669 (2021/04/05)
Employing silver/rhodium relay catalysis strategy, an intramolecular electrophilic cyclization and C?H activation followed by cascade hydrogenation and reductive amination has been developed. The acylmethylated isoquinoline derivatives could be afforded with broad substrate scope in 23–88% yields, which could be further transformed to the core skeleton of hexahydrodibenzo[a,g]quinolizine as drug-candidates. Moreover, this reaction was achieved in a gram-scale. A reasonable reaction mechanism has been proposed based on a series of control and KIE experiments. (Figure presented.).
NHC-Mediated Stetter-Aldol and Imino-Stetter-Aldol Domino Cyclization to Naphthalen-1(2 H)-ones and Isoquinolines
Barman, Debabrata,Ghosh, Tanmoy,Show, Krishanu,Debnath, Sudipto,Ghosh, Tapas,Maiti, Dilip K.
supporting information, p. 2178 - 2182 (2021/04/05)
N-Heterocyclic carbene-catalyzed tandem Stetter-aldol reaction of phthalaldehyde and α,β-unsaturated ketimines has been developed to afford functionalized naphthalen-1(2H)-one derivatives as the formal [4+2] annulation product. Interestingly, the reaction of aldimines led to the formation of isoquinoline derivatives instead of the expected indanone derivatives as a [4+1] annulation product.
