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One‐pot Synthesis of Isoquinoline‐Fused Isoquinolines via Intramolecular Hydroamination/Aza‐Claisen Type Rearrangement Cascade
Author(s) -
Chiu WeiJung,
Chen JinYu,
Liu ShihI,
Barve Indrajeet J.,
Huang WanWen,
Sun ChungMing
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202001576
Subject(s) - isoquinoline , hydroamination , chemistry , intramolecular force , claisen rearrangement , combinatorial chemistry , organic chemistry
A one‐pot, two‐step synthesis of isoquinoline‐fused isoquinolines from α‐amino acid esters and 2‐alkynyl benzaldehydes are reported. The strategy comprises an unconventional Pictet‐Spengler reaction between α‐amino acid esters and 2‐alkynyl benzaldehydes to give isoquinoline intermediates. Subsequent gold‐catalyzed intramolecular hydroamination furnishes isoquinoline‐fused isoquinolines. The scope of this strategy is further extended to prepare multisubstituted isoquinoline‐fused isoquinolines via subjecting the N‐allylated isoquinoline intermediates to gold‐catalyzed intramolecular hydroamination followed by aza‐Claisen type rearrangement.