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(a) Stein, R. P.; Delecki, D. J. US 4129561, 1979; Chem. Abstr. 1979, 90, 152035
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García, A.1
Paz, S.2
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8
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0000286496
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For a related cyclization of carbamates to simple 2-benzazepines, see: (a) Sánchez, I. H.; López, F. J.; Soria, J. J.; Larraza, M. I.; Flores, H. J. J. Am. Chem. Soc. 1983, 105, 7640.
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Sánchez, I.H.1
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Soria, J.J.3
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Flores, H.J.5
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9
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8644286981
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(b) Sánchez, I. H.; Larraza, M. I.; Flores, H. J.; Martell, E. A.; Linzaga, I.; Carter, A. A. Heterocycles 1985, 23, 251.
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Sánchez, I.H.1
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Flores, H.J.3
Martell, E.A.4
Linzaga, I.5
Carter, A.A.6
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10
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8644282262
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note
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All new compounds were fully characterized spectroscopically and had satisfactory elemental analyses or HRMS data.
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11
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Filippatos, E.; Papadaki-Valiraki, A.; Roussakis, C.; Verbist, J. F. Arch. Pharm. (Weinheim, Ger.) 1993, 326, 451.
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Verbist, J.F.4
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13
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0010162574
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Although the Bischler-Napieralski cyclization of secondary formamides is very effective for the formation of six-membered rings, it is generally less useful for the synthesis of 2-benzazepines, low yields having frequently been reported: (a) Alonso, R.; Takahashi, K.; Schönenberger, B.; Brossi, A. Heterocycles 1987, 26, 1595.
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Alonso, R.1
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14
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0009488207
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(b) Bird, C. W.; Brown, A. L.; Chan, C. C.; Lewis, A. Tetrahedron Lett. 1989, 30, 6223.
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Bird, C.W.1
Brown, A.L.2
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15
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0025091870
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(c) Clark, R. D.; Weinhardt, K. K.; Berger, J.; Fisher, L. E.; Brown, C. M.; MacKinnon, A. C.; Kilpatrick, A. T.; Spedding, M. J. Med. Chem. 1990, 33, 633.
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Clark, R.D.1
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Brown, C.M.5
MacKinnon, A.C.6
Kilpatrick, A.T.7
Spedding, M.8
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16
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37049067873
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Banwell, M. G.; Bissett, B. D.; Busato, S.; Cowden, C. J.; Hockless, D. C. R.; Holman, J. W.; Read, R. W.; Wu, A. W. J. Chem. Soc., Chem. Commun. 1995, 2551.
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Banwell, M.G.1
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Cowden, C.J.4
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Holman, J.W.6
Read, R.W.7
Wu, A.W.8
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17
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0037043540
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Some recent examples of electrophilic cyclization of carbamates leading to isoquinolones: (a) Wang, Y. C.; Georghiou, P. E. Org. Lett. 2002, 4, 2675.
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Org. Lett.
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Wang, Y.C.1
Georghiou, P.E.2
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0035085223
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(b) Kakefuda, A.; Watanabe, T.; Takahashi, T.; Sakamoto, S.; Tsukamota, S. I. Synth. Commun. 2001, 31, 401.
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Kakefuda, A.1
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Sakamoto, S.4
Tsukamota, S.I.5
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19
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0035906045
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(c) Pampin, M. C.; Estévez, J. C.; Castedo, L.; Estévez, R. J. Tetrahedron Lett. 2001, 42, 2307.
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Pampin, M.C.1
Estévez, J.C.2
Castedo, L.3
Estévez, R.J.4
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20
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0034647544
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(d) Banwell, M. G.; Harvey, J. E.; Hockless, D. C. R.; Wu, A. W. J. Org. Chem. 2000, 65, 4241.
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Wu, A.W.4
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21
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0034641477
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(e) Treus, M.; Estévez, J. C.; Castedo, L.; Estévez, R. J. Tetrahedron Lett. 2000, 41, 6351.
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Treus, M.1
Estévez, J.C.2
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Estévez, R.J.4
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22
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8644223538
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A 15% yield has been reported in the cyclization of a secondary carbamate: Potapov, V. M.; Dem'yanovich, V. M.; Solov'eva, L. D.; Vendrova, O. E. Khim. Geterotsikl. Soedin. 1981, 5, 675; Chem. Abstr. 1981, 95, 132135.
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Potapov, V.M.1
Dem'yanovich, V.M.2
Solov'eva, L.D.3
Vendrova, O.E.4
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23
-
-
8644286980
-
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A 15% yield has been reported in the cyclization of a secondary carbamate: Potapov, V. M.; Dem'yanovich, V. M.; Solov'eva, L. D.; Vendrova, O. E. Khim. Geterotsikl. Soedin. 1981, 5, 675; Chem. Abstr. 1981, 95, 132135.
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Chem. Abstr.
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-
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-
24
-
-
8644287723
-
-
note
-
+ - OMe]: 306.1494; found: 306.1502.
-
-
-
-
25
-
-
84985283644
-
-
Tertiary amides, which cannot form nitrilium ions under the Bischler-Napieralski reaction conditions, are known not to afford seven-membered rings under these conditions: Schlüter, G.; Meise, W. Liebigs Ann. Chem. 1988, 833.
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Liebigs Ann. Chem.
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Schlüter, G.1
Meise, W.2
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26
-
-
46549103031
-
-
Cyclization by intramolecular amidoalkylation of aromatics with reactive N-acyliminium ions allows the synthesis of a variety of benzofused heterocyclic systems: (a) Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367.
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Tetrahedron
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Speckamp, W.N.1
Hiemstra, H.2
-
28
-
-
8644285280
-
-
note
-
3: C, 74.75; H, 5.96; N, 4.36. Found: C, 74.57; H, 5.77; N, 4.41.
-
-
-
-
29
-
-
0034743059
-
-
and references therein
-
(a) There are only a few known examples of N-acyliminium cyclizations leading to seven-membered benzofused heterocycles: Bahajaj, A. A.; Vernon, J. M.; Wilson, G. D. J. Chem. Soc., Perkin Trans. 1 2001, 1446; and references therein.
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J. Chem. Soc., Perkin Trans. 1
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Bahajaj, A.A.1
Vernon, J.M.2
Wilson, G.D.3
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30
-
-
0037423153
-
-
(b) For a related cyclization leading to a 5-7-6 tricyclic aza-analogue, see: Marson, C. M.; Pink, J. H.; Hall, D.; Hursthouse, M. B.; Malik, A.; Smith, C. J. Org. Chem. 2003, 68, 792.
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Marson, C.M.1
Pink, J.H.2
Hall, D.3
Hursthouse, M.B.4
Malik, A.5
Smith, C.6
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