Smooth isoindolinone formation from isopropyl carbamates via Bischler-Napieralski-type cyclization

Satoshi Adachi; Masao Onozuka; Yuko Yoshida; Mitsuaki Ide; Yoko Saikawa; Masaya Nakata

doi:10.1021/ol403142d

Smooth isoindolinone formation from isopropyl carbamates via Bischler-Napieralski-type cyclization

Org Lett. 2014 Jan 17;16(2):358-61. doi: 10.1021/ol403142d. Epub 2013 Dec 23.

Authors

Satoshi Adachi¹, Masao Onozuka, Yuko Yoshida, Mitsuaki Ide, Yoko Saikawa, Masaya Nakata

Affiliation

¹ Department of Applied Chemistry, Faculty of Science and Technology, Keio University , 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.

PMID: 24364475
DOI: 10.1021/ol403142d

Abstract

Isopropyl carbamates derived from benzylamines provide isoindolinones by treatment with phosphorus pentoxide at room temperature. Utility of this Bischler-Napieralski-type cyclization and a new mechanism involving a carbamoyl cation for rationalization of this smooth conversion are discussed.

Publication types

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

MeSH terms

2-Propanol / chemistry
Benzylamines / chemistry*
Carbamates / chemistry*
Cyclization
Esters
Indoles / chemical synthesis*
Indoles / chemistry
Molecular Structure
Phosphorus Compounds / chemistry
Temperature

Substances

Benzylamines
Carbamates
Esters
Indoles
Phosphorus Compounds
phosphorus pentoxide
2-Propanol