A simple approach to bis-spirocycles and spiroindole derivatives via greenmethods such as Fischer indolization, ring-closing metathesis, andSuzuki{Miyaura cross-coupling
A simple approach to bis-spirocycles and spiroindole derivatives via greenmethods such as Fischer indolization, ring-closing metathesis, andSuzuki{Miyaura cross-coupling
We have developed a simple synthetic methodology for bis-spirocycles and spiroindole derivatives startingwith a commercially available 6-bromo-2-tetralone. Here, we have used Fischer indolization, ring-closing metathesis, andSuzuki{Miyaura cross-coupling as key steps to assemble a variety of spirocyclic frameworks. The methodology developedhere is simple and it may be useful to prepare various spirocycles containing indole moiety
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- 1.Kotha, S.; Lahiri, K.; Kashinath, D.Tetrahedron2002,58, 9633{9695.
- 2.Suzuki, A. J.Organomet. Chem.1997,36, 2163{2187.
- 3.Littke, A. F.; Dai, C.; Fu, G. C.J. Am. Chem. Soc.2000,122, 4020{4028.
- 4.Kotha, S.; Lahiri, K.Eur. J. Org. Chem.2007,2007, 1221{1236.
- 5.Kotha, S.; Mandal, K.Chem. Asian. J.2009,4, 354{362.
- 6.Kotha, S.; Lahiri, K.Bioorg Med. Chem. Lett.2001,11, 2887{2890.
- 7.Kasai, Y.; Ito, T.; Sasaki, M.Org. Lett.2012,14, 3186{3189.
- 8.Corbet, J. P.; Mignani, G.Chem. Rev.2006,106, 2651{2710.
- 9.Liu, L.; Zhang, Y.; Xin, B.J. Org. Chem.2006,71, 3994{3997.
- 10.Hamilton, A. E.; Buxton, A. M.; Peeples, C. J.; Chalker, J. M.J. Chem. Educ.2013,90, 1509{1513.
- 11.Keese, R.Chem. Rev.2006,106, 4787{4808.12.Rosenberg, S.; Leino, R.Tetrahedron Lett.2009,50, 5305{5307.
- 13.George, S. C.; John, J.; Anas, S.; John, J.; Yamamoto, Y.; Suresh, E.; Radhakrishnan, K. V.Eur. J. Org. Chem.2010,2010, 5489{5497.
- 14.Oblak, E. Z.; Dayanandan, N. G.; Wright, D. L.Org. Lett.2011,13, 2433{2435.
- 15.Kotha, S.; Deb, A. C.; Lahiri, K.; Manivannan, E.Synthesis2009, 165{193.
- 16.Kotha, S.; Deb, A. C.; Vinodkumar, R.Bioorg. Med. Chem. Lett.2005,15, 1039{1043.
- 17.Kotha, S.; Mandal, K.; Mandal, K.; Deb, A. C.; Banerjee, S.Tetrahedron Lett.2004,45, 9603{9605.
- 18.Kotha, S.; Mandal, K.Tetrahedron Lett.2004,45, 1391{1394.
- 19.Kotha, S.; Ali, R.; Chinnam, A. K.Tetrahedron Lett.2014,55, 4492{4495.
- 20.Liang, J. J.; Pan, J. Y.; Xu, D. C.; Xie, J. W.Tetrahedron Lett.2014,55, 6335{6338.
- 21.Huang, J.; Frontier, A. J.J. Am. Chem. Soc.2007,129, 8060{8061.
- 22.Sawada, T.; Nakada, M.Org. Lett.2013,15, 1004{1007.
- 23.Carreira, E. M.; Fessard, T. C.Chem. Rev.2014,114, 8257{8322.
- 24.Kurhade, S. E.; Sanchawala, A. I.; Ravikumar, V.; Bhuniya, D.; Reddy, D. S.Org. Lett.2011,13, 3690{3693.
- 25.Mori, M.Materials2010,3, 2087{2140.
- 26.Kotha, S.; Shah, V. R.; Mandal, M.Adv. Synth. Catal.2007,349, 1159{1172.
- 27.Kotha, S.; Dipak, M. K.Chem. Eur. J.2006,12, 4446{4450.
- 28.Kotha, S.; Chavan, A. S.; Mobin, S.J. Org. Chem.2012,77, 482{489.
- 29.Kotha, S.; Ali, R.; Tiwari, A.Synlett2013, 1921{1926.
- 30.Kotha, S.; Ali, R.; Tiwari, A.Synthesis2014, 2471{2480.
- 31.Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H.Org. Lett.1999,1, 953{956.
- 32.Maier, M. E.Angew. Chem. Int. Ed.2000,39, 2073{2077.
- 33.Samojlowicz, C.; Bieniek, M.; Grela, K.Chem. Rev.2009,109, 3708{3742.
- 34.Kotha, S.; Meshram, M.; Tiwari, A.Chem. Soc. Rev.2009,38, 2065{2092.
- 35.Vougioukalakis, G. C.; Grubbs, R. H.Chem. Rev.2010,110, 1746{1787.
- 36.Kotha, S.; Dipak, M. K.Tetrahedron2012,68, 397{421.
- 37.Deiters, A.; Martin, S. F.Chem. Rev.2004,104, 2199{2238.
- 38.Sannigrahi, M.Tetrahedron1999,55, 9007{9071.
- 39.Santos, M. M. M.Tetrahedron2014,70, 9735{9757.
- 40.Undheim, K.Synthesis2014, 1957{2006.
- 41.Kotha, S.; Ali, R.; Srinivas, V.; Krishna, N. G.Tetrahedron2015,71, 129{138.
- 42.Gritsch, P. J.; Stempel, E.; Gaich, T.Org. Lett.2013,15, 5472{5475.
- 43.Chen, Y.; Wang, Y.; Sun, Z.; Ma, D.Org. Lett.2008,10, 625{628.
- 44.Bajtos, B.; Pagenkopf, B. L.Org. Lett.2009,11, 2780{2783.
- 45.Humphrey, G. R.; Kuethe, J. T.Chem. Rev.2006,106, 2875{2911.
- 46.Shiri, M.Chem. Rev.2012,112, 3508{3549.
- 47.Cacchi, S.; Fabrizi, G.Chem. Rev.2005,105, 2873{2920.
- 48.Schmidt, A. W.; Reddy, K. R.; Knolker, H. J.Chem. Rev.2012,112, 3193{3328.
- 49.Deiters, A.; Martin, S. F.Org. Lett.2002,4, 3243{3245.
- 50.Kochanowska-Karamyan, A. J.; Hamann, M. T.Chem. Rev.2010,110, 4489{4497.
- 51.Galliford, C. V.; Scheidt, K. A.Angew. Chem. Int. Ed.2007,46, 8748{8758.
- 52.Trost, B. M.; Brennan, M. K.Synthesis2009, 3003{3025.
- 53.Li, C.; Gloer, J. B.; Wicklow, D. T.; Dowd, P. F.Org. Lett.2002,4, 3095{3098.
- 54.Lounasmaa, M.; Tolvanen, A.Nat. Prod. Rep.2000,17, 175{191.
- 55.Lewis, S. E.Tetrahedron2006,62, 8655{8681.
- 56.Higuchi, T.; Kawasaki, T.Nat. Prod. Rep.2007,24, 843{868.1198