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Synthesis 2003(18): 2839-2843
DOI: 10.1055/s-2003-42448
DOI: 10.1055/s-2003-42448
PAPER
© Georg Thieme Verlag Stuttgart · New York
A Simple One-Pot Reaction to the Bis-dibenzo[b,f][1,5]diazocines: Useful Precursors of Novel Macrocycles
Further Information
Received
5 August 2003
Publication Date:
23 October 2003 (online)
Publication History
Publication Date:
23 October 2003 (online)
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’
- 1
Meth-Cohn O.Taylor DL. J. Chem. Soc., Chem. Commun. 1995, 1463 - 2
Cheng Y.Meth-Cohn O.Taylor DL. J. Chem. Soc., Perkin Trans. 1 1998, 1257 - 3
Cheng Y.Liu Q.-X.Meth-Cohn O. Tetrahedron Lett. 2000, 41: 3475 - 4
Crossley R.Downing AP.Nogradi M.Braga de Oliviera A.Ollis WD.Sutherland IO. J. Chem. Soc. Perkin Trans. 1 1973, 205 - 5
Cheng Y.Yang H.-B.Liu B.Meth-Cohn O.Watkin D.Humphries S. Synthesis 2002, 906 - 6
Cheng Y.Liu Q.-X.Meth-Cohn O. Synthesis 2000, 640 - 7
Meth-Cohn O. Adv. Heterocycl. Chem. 1996, 65: 1 - 8
Roberts RM.Vogt PJ. Org. Synth, Coll. Vol. 4: Wiley; New York: 1963. p.420 - 9
Sheppard WA. Org. Synth., Coll. Vol. 5: Wiley; New York: 1973. p.1085