The Formation of Seven-Membered Heterocycles under Mild Pictet-Spengler Conditions: A Route to Pyrazolo[3,4]benzodiazepines

Timothy A Katte; Tristan A Reekie; William T Jorgensen; Michael Kassiou

doi:10.1021/acs.joc.6b00710

The Formation of Seven-Membered Heterocycles under Mild Pictet-Spengler Conditions: A Route to Pyrazolo[3,4]benzodiazepines

J Org Chem. 2016 Jun 3;81(11):4883-9. doi: 10.1021/acs.joc.6b00710. Epub 2016 May 13.

Authors

Timothy A Katte¹, Tristan A Reekie¹, William T Jorgensen¹, Michael Kassiou¹

Affiliation

¹ School of Chemistry, The University of Sydney , Sydney, New South Wales 2006, Australia.

PMID: 27159074
DOI: 10.1021/acs.joc.6b00710

Abstract

Reported is a method for the synthesis of seven-membered heterocycles via a Pictet-Spengler condensation reaction under very mild conditions. High substrate scope allows for use of aldehydes using catalytic amounts of acetic acid yielding 39-90% and ketones using catalytic amounts of trifluoroacetic acid yielding 25-83%.

Publication types

Research Support, Non-U.S. Gov't