Synthesis of 1‐amino‐4‐chloroisoquinoline. A new approach to 1‐aminoisoquinoline

Abstract

The as yet unknown 1‐amino‐4‐chloroisoquinoline was synthesised from 1,4‐dichloroisoquinoline through the 1‐phenoxy‐4‐chloro derivative. This procedure was also suitable for obtaining 1‐aminoisoquinoline from 1‐chloroisoquinoline in good yields.

Selective urokinase-type plasminogen activator (uPA) inhibitors. Part 3: 1-Isoquinolinylguanidines

“…The 1-chloro intermediates were either known compounds (4-CH 3 , 12 5-OCH 3 , 12 7-OCH 3 , 12 4-Cl, 13 4-Br, 14 5-Br 15 ) or were prepared from the corresponding isoquinoline by oxidation with either 30% H 2 O 2 /AcOH or mCPBA/CH 2 Cl 2 , followed by treatment of the N-oxide with POCl 3 (5-C 6 H 5 , 16 5-OCH 2 C 6 H 5 , 17 6-Br, 18 7-OCH 2 C 6 H 5 19 ). In the case of 5-bromo-1-chloro-and 7-bromo-1-chloroisoquinolines, a mixture of 5-and 7-bromoisoquinoline 20 was oxidized, the product was treated with POCl 3 and the mixture of chloro compounds was separated by fractional crystallization from THF at )78°C to give the individual isomers 3e and 3j (Scheme 2).…”

Design, Syntheses and Biological Evaluations of Nonpeptidic Caspase 3 Inhibitors

“…1-Phenoxyisoquinoline (52) 31 Molecular Modeling. All procedures were performed using SYBYL (v. 6.7, Tripos Associate Inc.) operating under Origin R100.…”