A Simple One-Pot Reaction to the Bis-dibenzo[b,f][1,5]diazocines: Useful Precursors­ of Novel Macrocycles

Ying Cheng; Bo Wang; Otto Meth-Cohn

doi:10.1055/s-2003-42448

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A Simple One-Pot Reaction to the Bis-dibenzo[b,f][1,5]diazocines: Useful Precursors of Novel Macrocycles

Ying Cheng*^a, Bo Wang^a, Otto Meth-Cohn^b
^a Department of Chemistry, Beijing Normal University, Beijing 100875, P. R. China
e-Mail: yingcheng1@263.net;
^b Chemistry Department, Sunderland University, Sunderland, UK SR1 3SD, UK

Abstract

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Abstract

The title compounds, namely 8,8′-bis-5,6,11,12-tetrahydrodibenzo[b,f][1,5]diazocines, have been synthesized in 36-81% yields through a one-pot reaction by treatment of N,N,N′,N′-tetramethylbiphenyldiamine with the Vilsmeier’s reagents derived from substituted N-methylformanilides and POCl₃. This was another application of ‘t-amino effect’ in the synthesis of eight-membered ring systems. These products are designed as the precursors of novel macrocycles.

Key words

8,8′-bis-5,6,11,12-tetrahydrodibenzo[b,f][1,5]diazocines - N,N,N′,N′-tetramethylbiphenyldiamine - N-methylformanilides - Vilsmeier’s reagent - ‘t-amino effect’

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A Simple One-Pot Reaction to the Bis-dibenzo[b,f][1,5]diazocines: Useful Precursors­ of Novel Macrocycles

A Simple One-Pot Reaction to the Bis-dibenzo[b,f][1,5]diazocines: Useful Precursors of Novel Macrocycles