Synthesis of 3-indolylimines from 3-acetamido-2-phenylindole. Issue 23 (5th June 2020)

• Record Type: Journal Article
• Authors: Qu, Ji; Wenholz, Daniel S.; Kumar, Naresh; Black, David StC.
• Is Part Of: Tetrahedron. Volume 76:Issue 23(2020)
• Publication Date: 2020-06-05
• Subjects: Indoles -- 3-Aminoindoles -- 3-Amidoindoles -- Iminium chlorides -- N-indolylketimines; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2020.131224
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: © 2020 Elsevier Science. All rights reserved Treatment of 3-acetamido-2-phenylindole with phosphoryl chloride generates an iminium chloride (or related) electrophile that can react with suitable indole nucleophiles at C3, C7 or C2 to form di-indolylketimines in moderate yield. Similar reactions of the diacetyl derivative of 2-aminobenzylalcohol give related mono-indolylketimines. Graphical abstract: Image 1 Highlights: Iminium chlorides are effective reagents for formation of imines. 3-Amidoindoles are very effective starting materials for formation of di-(3-indolyl)imines. New di-indolylimine chromophores have been synthesized. Methoxy substituents at C4 and C6 activate indoles to react at C7 and form new structures. This synthetic methodology is very general and provides opportunities for wider development.