Efficient Synthesis of 1,3,5-Benzotriazocines from Tetrachloro-2-aza-1,3-dienes

Abstract

Easily accessible 1-aryl-2-aza-1,3-butadienes undergo a regioselective cyclocondensation with 2-(aminomethyl)aniline, giving rise to 1,3,5-benzotriazocines in good yields. The structure of the title compounds was proved with the aid of ¹H and ¹³C NMR spectra and, in one case, single-crystal x-ray analysis.

[Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.]

GRAPHICAL ABSTRACT

Keywords:

• 2-(Aminomethyl)aniline
• 1,3,5-benzotriazocine
• heterocyclization
• regioselective cyclocondensation
• tetrachloro-2-aza-1,3-dienes