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The Vilsmeier formylation has also been applied to alkenes, acetals, and ketals, see: Smith, M. B.; March, J. Advanced Organic Chemistry, 5th ed.; J. Wiley & Sons: New York, 2001; p 785 and references therein.
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For recent reviews on cruciferous phytoalexins see: (a) Pedras, M. S. C.; Okanga, F. I.; Zaharia, I. L.; Khan, A. Q. Phytochemistry 2000, 53, 161. (b) Pedras, M. S. C.; Jha, M.; Ahiahonu, P. W. K. Curr. Org. Chem. 2003, 7, 1635.
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Pedras, M.S.C.1
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Khan, A.Q.4
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7
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For recent reviews on cruciferous phytoalexins see: (a) Pedras, M. S. C.; Okanga, F. I.; Zaharia, I. L.; Khan, A. Q. Phytochemistry 2000, 53, 161. (b) Pedras, M. S. C.; Jha, M.; Ahiahonu, P. W. K. Curr. Org. Chem. 2003, 7, 1635.
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Pedras, M.S.C.1
Jha, M.2
Ahiahonu, P.W.K.3
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8
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0024519185
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Indolin-2-ones have been used to prepare of GABAergic agents; see, for example: Sarges, R.; Howard, H. R.; Koe, B. K.; Weissman, A. J. Med. Chem. 1989, 32, 437.
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Sarges, R.1
Howard, H.R.2
Koe, B.K.3
Weissman, A.4
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9
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0029035467
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Indoline-2-thiones are also useful in the preparation of tyrosine kinase inhibitors, i.e., the corresponding 3-substituted 2,2′-dithiobis-(1H- indoles); see, for example: Palmer, B. D.; Rewcastle, G. W.; Thompson, A. M.; Boyd, M.; Showalter, H. D. H.; Sercel, A. D.; Fry, D. W.; Kraker, A. J.; Denny, W. A. J. Med. Chem. 1995, 38, 58.
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Palmer, B.D.1
Rewcastle, G.W.2
Thompson, A.M.3
Boyd, M.4
Showalter, H.D.H.5
Sercel, A.D.6
Fry, D.W.7
Kraker, A.J.8
Denny, W.A.9
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11
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3042739832
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Pedras, M. S. C.; Montaut, S.; Suchy, M. J. Org. Chem. 2004, 69, 4471.
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Pedras, M.S.C.1
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Suchy, M.3
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Pedras, M. S. C.; Zaharia, I. L.; Gai, Y.; Zhou, Y.; Ward, D. E. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 747.
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Pedras, M.S.C.1
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Zhou, Y.4
Ward, D.E.5
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15
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(a) Rouxel, T.; Kollmann, A.; Boulidard, L.; Mithen, R. Planta 1991, 184, 271.
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Rouxel, T.1
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(b) Pedras, M. S. C.; Nycholat, C. M.; Montaut, S.; Xu, Y.; Khan, A. Q. Phytochemistry 2002, 59, 611.
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0142026148
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Pedras, M. S. C.; Chumala, P. B.; Suchy, M. Phytochemistry 2003, 64, 949.
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Chumala, P.B.2
Suchy, M.3
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18
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84989444646
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Indoline-2-thione was prepared following a general procedure for conversion of the carbonyl group to the thione group: Scheeren, J. W.; Ooms, P. H. J.; Nivard, R. J. F. Synthesis 1973, 149.
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19
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14544268656
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note
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2.
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-
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20
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14544306148
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note
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Although the results shown in Table 1 entry 6 represented an improvement in the yield of 12, due to the amount of starting material remaining in the reaction mixture, the additional chromatographic separation required rendered this preparation less efficient.
-
-
-
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21
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14544271985
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note
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A number of undetermined products were formed including 2-chloroindole-3-carbaldeheyde (11) in ca. 10%.
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-
-
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22
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14544286488
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note
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Compound 21 was synthesized using the conditions of entry 8, Table 1 followed by water workup instead of ammonia.
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-
-
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23
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14544278474
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note
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For complete spectroscopic data of 19, see ref 8.
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-
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25
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3242698936
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Goetz, F. J.; Hirsch, J. A.; Augustine, R. L. J. Org. Chem. 1983, 48, 2468.
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Goetz, F.J.1
Hirsch, J.A.2
Augustine, R.L.3
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27
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14544292551
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note
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Described in the Supporting Information.
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-
-
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28
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0026184366
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Compound 24a was previously prepared using a different procedure and undisclosed yield; see: Tempete, C.; Devys, M.; Barbier, M. Z. Naturforsch., C: J. Biosci. 1991, 46, 706.
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Tempete, C.1
Devys, M.2
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31
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Robertson, D. W.; Krushinski, J. H.; Kau, D. J. Labelled Compd. Radiopharm. 1986, 23, 343.
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Robertson, D.W.1
Krushinski, J.H.2
Kau, D.3
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32
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14544268655
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Compound 27d was prepared previously using Vilsmeier conditions in 30% yield; see: Andreani, A.; Bonazzi, D.; Rambaldi, M.; Mungiovino, G.; Greci, L. Farmaco 1978, 33, 781.
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Andreani, A.1
Bonazzi, D.2
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Mungiovino, G.4
Greci, L.5
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33
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14544301523
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note
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3CN solution as a mixture of E/Z isomers (spectroscopic data in the Supporting Information).
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35
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0003412412
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J. Wiley & Sons: New York
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The reaction of ammonia with aldehydes leads to spontaneous polymerization of the resulting imines. (a) Smith, M. B.; March, J. Advanced Organic Chemistry, 5th ed.; J. Wiley & Sons: New York, 2001; p 1186. (b) Hull, W. E.; Sykes, B. D.; Babior, B. M. J. Org. Chem. 1973, 38, 2931.
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0041863430
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The reaction of ammonia with aldehydes leads to spontaneous polymerization of the resulting imines. (a) Smith, M. B.; March, J. Advanced Organic Chemistry, 5th ed.; J. Wiley & Sons: New York, 2001; p 1186. (b) Hull, W. E.; Sykes, B. D.; Babior, B. M. J. Org. Chem. 1973, 38, 2931.
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Hull, W.E.1
Sykes, B.D.2
Babior, B.M.3
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0035855317
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Rewcastle, G. W.; Janosik, T.; Bergman, J. Tetrahedron 2001, 57, 7185.
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