An efficient route to <i>N</i>-alkylated 3,4-dihydroisoquinolinones with substituents at the 3-position

Tazawa, Aoi; Ando, Junki; Ishizawa, Kohei; Azumaya, Isao; Hikawa, Hidemasa; Tanaka, Minoru

doi:10.1039/c7ra13627g

Cited by 4 publications

(1 citation statement)

References 26 publications

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“…This strategy involve synthesis of the iminium salt 213 by alkylation of the imine 212 followed by oxidation using K 4 Fe (CN) 6 to get dihydroisoquinolinones in good yield as per the reaction sequence depicted in Scheme 80. [96] The synthesis of the imine 212 is achieved as per the reaction sequence depicted in Scheme 81.…”

Section: Scheme 42 Synthesis 4-hydroxyalkyl-substituted 34-dihydroimentioning

confidence: 99%

Recent Advances in Synthesis of 3,4‐Dihydroisoquinolin‐1(2H)‐one

Kulkarni

Gaikwad

2020

ChemistrySelect

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The 3,4‐dihydroisoquinolin‐1(2H)‐one motifs found in many natural products, synthetic molecules with a diverse range of the biological activities and represent a privilege scaffold. Thereby the number of the innovative synthetic methodologies has been reported for constructions of this scaffold, which includes metal catalyzed and metal free method, multicomponent, domino one pot protocol, oxidation, Friedel‐Crafts type of cyclization. In the recent years many general protocols for the construction of this scaffold were reported in the literature and there is no focussed individual review for the 3,4‐dihydroisoquinolin‐1(2H)‐one since 2001. This review focuses on the reports describing the new method for the synthesis of 3,4‐dihydroisoquinolin‐1(2H)‐one, published since 2001 to till date. In this review, we approach method of the synthesis of 3,4‐dihydroisoquinolin‐1(2H)‐one according to the strategy used for its synthesis, which includes, the intramolecular cyclization of carbamate/ urea/ thiourea/ isocyanate/ azidoamide, carbonylation/ carbomylation/ carbonyl insertion, metal catalyzed protocols by C−H activation by directing group, metal free domino procedures and oxidations of isoquinoline derivatives that were included in recent publications. Moreover, the reports published since 2001 for the synthesis of the chiral 3,4‐dihydroisoquinolin‐1(2H)‐one are included.

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Section: Scheme 42 Synthesis 4-hydroxyalkyl-substituted 34-dihydroimentioning

confidence: 99%