Synthesis, Inhaltsverzeichnis Synthesis 2017; 49(18): 4321-4326DOI: 10.1055/s-0036-1588181 paper © Georg Thieme Verlag Stuttgart · New YorkSc(OTf)3-Catalyzed Oligomerization of Indole: One-Pot Synthesis of 2-[2,2-Bis(indol-3-yl)ethyl]anilines and 3-(Indolin-2-yl)indoles Ganesh M. Shelke Department of Chemistry, Birla Institute of Technology and Science, Pilani, Rajasthan 333031, India eMail: anilkumar@pilani.bits-pilani.ac.in , Anil Kumar * Department of Chemistry, Birla Institute of Technology and Science, Pilani, Rajasthan 333031, India eMail: anilkumar@pilani.bits-pilani.ac.in› InstitutsangabenArtikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract Oligomerization of substituted indoles and N-methylindoles was investigated in the presence of catalytic amounts of scandium triflate in dichloromethane. Two types of indole oligomer, 2-[2,2-bis(indol-3-yl)ethyl]anilines and 3-(indolin-2-yl)indoles were obtained based on the substituent on indole ring. This study constitutes the first example of Sc(OTf)3-catalyzed oligomerization of indoles and gave good yield of 2-[2,2-bis(indol-3-yl)ethyl]anilines and 3-(indolin-2-yl)indoles. Key words Key wordsoligomerization - scandium triflate - bis(indolyl)methanes - indole - dimer - trimer Volltext Referenzen References 1a Joule JA. Mills K. Heterocyclic Chemistry . 4th ed. Blackwell Science; Oxford: 2000 1b Sundberg RJ. The Chemistry of Indoles. Academic Press; New York: 1996: 7 1c Faulkner DJ. Nat. Prod. Rep. 2001; 18: 1 1d Ishikura M. Yamada K. Nat. Prod. Rep. 2009; 26: 803 2a Wu Y.-H. Lobeck WG. Ryan RP. Gomoll AW. J. Med. Chem. 1972; 15: 529 2b Osawa T. Namiki M. Tetrahedron Lett. 1983; 24: 4719 2c Bell R. Carmeli S. Sar N. J. Nat. Prod. 1994; 57: 1587 2d Khuzhaev BU. Aripova SF. Shakirov RS. Chem. Nat. Compd. 1994; 30: 635 2e Veluri R. Oka I. Wagner-Döbler I. Laatsch H. J. Nat. Prod. 2003; 66: 1520 2f Chintharlapalli S. Papineni S. Safe S. Mol. Cancer Ther. 2006; 5: 1362 2g Noland WE. Vijay Kumar H. Lu C. Brown CD. Wiley-Schaber E. Johansson A. LaBelle EV. O’Brian NC. Jensen RC. Tritch KJ. Tetrahedron Lett. 2016; 57: 2158 3a Shiri M. Zolfigol MA. Kruger HG. Tanbakouchian Z. Chem. Rev. 2010; 110: 2250 3b Shelke GM. Rao VK. Tiwari RK. Chhikara BS. Parang K. Kumar A. RSC Adv. 2013; 3: 22346 3c Mi X. Luo S. He J. Cheng J.-P. Tetrahedron Lett. 2004; 45: 4567 3d Yadav JS. Reddy BV. S. Praneeth K. Tetrahedron Lett. 2008; 49: 199 3e Chakrabarty M. Taraknath K. Yoshihiro H. J. Chem. Res. 2004; 778 3f Singh N. Singh KN. Synlett 2012; 23: 2116 3g Kottawar SS. Siddiqui SA. Pendalwar SS. Jadhav WN. Bhusare SR. Res. Chem. Intermed. 2014; 40: 2929 4a Smith GF. The Acid-Catalyzed Polymerization of Pyrroles and Indoles. In Advances in Heterocyclic Chemistry. Vol. 2: 2. Katritzky AR. Academic Press; New York: 1963: 87 4b Soylu O. Uzun S. Can M. Colloid Polym. Sci. 2011; 289: 903 5 Geller K. Ber. Bunsen-Ges. 1913; 46: 726 6 Smith GF. Chem. Ind. (London) 1954; 20: 1451 7 Ishii H. Murakami K. Murakami Y. Hosoya K. Chem. Pharm. Bull. 1977; 25: 3122 8 Chakrabarty M. Khasnobis S. Harigaya Y. Konda Y. Synth. Commun. 2000; 30: 187 9 Bocchi V. Palla G. Tetrahedron 1986; 42: 5019 10 Pal B. Sesha Giri V. Jaisankar P. Catal. Commun. 2005; 6: 711 11a Kobayashi S. Sugiura M. Kitagawa H. Lam WW. L. Chem. Rev. 2002; 102: 2227 11b Sakhuja R. Pericherla K. Bajaj K. Khungar B. Kumar A. Synthesis 2016; 48: 4305 12a Kobayashi S. Eur. J. Org. Chem. 1999; 15 12b Yadav JS. Reddy BV. S. Pandey SK. Srihari P. Prathap I. Tetrahedron Lett. 2001; 42: 9089 12c Yadav JS. Reddy BV. S. Parisse C. Carvalho P. Rao TP. Tetrahedron Lett. 2002; 43: 2999 12d Kuciński K. Pawluć P. Marciniec B. Hreczycho G. Chem. Eur. J. 2015; 21: 4940 13 Ishii H. Murakami K. Sakurada E. Hosoya K. Murakami Y. J. Chem. Soc., Perkin Trans. 1 1988; 2377 14 Kinthada LK. Ghosh S. De S. Bhunia S. Dey D. Bisai A. Org. Biomol. Chem. 2013; 11: 6984 15 Fujino K. Yanase E. Shinoda Y. Nakatsuka S.-i. Biosci., Biotechnol., Biochem. 2004; 68: 764 16 Schmitz-Dumont O. Nicolojannis B. Schnorrenberg E. Saenger HH. J. Prakt. Chem. 1931; 131: 146 Zusatzmaterial Zusatzmaterial Supporting Information
