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Synthesis 2002(16): 2393-2398
DOI: 10.1055/s-2002-35234
DOI: 10.1055/s-2002-35234
PAPER
© Georg Thieme Verlag Stuttgart · New York
Intramolecular [4 + 2] Cycloaddition Reactions of Ketenimines: A New Synthesis of Benz[b]acridines
Further Information
Received
18 July 2002
Publication Date:
04 November 2002 (online)
Publication History
Publication Date:
04 November 2002 (online)
Abstract
N-[2-(2-Propenyl)phenyl]-C,C-diphenyl ketenimines undergo a thermally induced intramolecular [4 + 2] cycloaddition to give 5,11,11a,12-tetrahydrobenz[b]acridines, which are converted into the fully aromatic benz[b]acridines by oxidation with Pd/C in refluxing ortho-xylene.
Key words
azides - acridines - cycloadditions - polycycles - ketenimines - phosphazenes
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1a
Barker MW.McHenry WE. In The Chemistry of Ketenes, Allenes and Related Compounds Part. 2:Patai S. Wiley; Chichester: 1980. p.701 -
1b
Alajarín M.Vidal A.Tovar F. Targets Heterocycl. Syst. 2000, 4: 293 ; and references cited therein. -
2a
Molina P.Alajarín M.Vidal A. Tetrahedron Lett. 1991, 32: 5379 -
2b
Molina P.Alajarín M.Vidal A. J. Org. Chem. 1992, 57: 6703 - 3
Alajarín M.Vidal A.Tovar F.Conesa C. Tetrahedron Lett. 1999, 40: 6127 - 4
Alajarín M.Vidal A.Tovar F. Tetrahedron Lett. 2000, 41: 7029 - General syntheses of benz[b]acridines have been scarcely reported and usually yield oxidized derivatives. For examples, see:
-
5a
Narasimhan NS.Ranade AC. Indian J. Chem. 1969, 7: 538 -
5b
Roushdi IM.Mikhail AA.Chaaban I. Pharmazie 1976, 31: 406 -
5c
Joos K.Pardo M.Schäfer W. J. Chem. Res., Synop. 1978, 406 -
5d
Hamdan AJ.Moore HW. J. Org. Chem. 1985, 50: 3427 -
5e
Chuang C.-P.Wu Y.-L.Jiang M.-C. Tetrahedron 1999, 55: 11229 -
5f
Prato M.Scorrano G.Stiranello M.Tecilla P.Lucchini V. Gazz. Chim. Ital. 1987, 117: 325 -
5g
Alvarez M.Ajana W.López-Calahorra F.Joule JA. J. Chem. Soc., Perkin Trans. 1 1994, 917 -
6a
Staudinger H.Meyer J. Helv. Chim. Acta 1919, 2: 635 -
6b
Gololobov YG.Kasukhin LF. Tetrahedron 1992, 48: 1353 -
6c
Gololobov YG.Zhmurova IN.Kasukhin LF. Tetrahedron 1981, 37: 437 - 7
Smith PAS.Chou SP. J. Org. Chem. 1981, 46: 3970 -
10a
Alkhader MA.Smalley RK.Mohajerani B. Synthesis 1980, 381 -
10b
Bassoli A.Maddinelli G.Rindone B.Tollari S.Chioccara F. J. Chem. Soc., Chem. Commun. 1987, 150 - 11
Taylor EC.McKillop A.Hawks GH. Org. Synth. 1973, 52: 36 - 12
Le Corre M.Hercouet A.Le Stanc Y.Le Baron H. Tetrahedron 1985, 41: 5313
References
Compound 2 31P NMR (121.4 MHz, CDCl3): δ = 1.29.
9The heating of the toluene solutions of the ketenimines 10 at 130 °C in a sealed tube gave mixtures of 5,11,11a,12-tetrahydro, 5,12-dihydro and the fully aromatic 11-aryl-6-phenylbenz[b]acridines, and the same results were obtained when this thermal treatment was carried out in the presence of Pd/C.