Facile synthesis of 2-arylmethylindoles and 2-vinylic indoles through palladium-catalyzed heteroannulations of 2-(2-propynyl)aniline and 2-(2-propynyl)tosylanilide

作者: Bimolendu Das , Priyanka Kundu , Chinmay Chowdhury

DOI: 10.1039/C3OB41961D

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摘要: A facile method for the general synthesis of 2-arylmethylindoles has been developed through reaction 2-(2-propynyl)aniline or 2-(2-propynyl)tosylanilide with aryl iodides in presence Pd(OAc)2, PPh3, and DBU. 2-(2-Propynyl)tosylanilide is found to be reactive also towards electron deficient alkenes Pd(OAc)2 sodium iodide under an oxygen atmosphere, providing easy access 2-vinylic indoles which possess exclusive E-stereochemistry side chain double bond. Operational simplicity, compatibility various functional groups, ease product formation are hallmarks these methods. mechanism proposed explain formation.

参考文章(70)
Vikas Sharma, Pradeep Kumar, Devender Pathak, Biological importance of the indole nucleus in recent years: A comprehensive review Journal of Heterocyclic Chemistry. ,vol. 47, pp. 491- 502 ,(2010) , 10.1002/JHET.349
Larissa B Wolf, Kim CMF Tjen, Hefziba T ten Brink, Richard H Blaauw, Henk Hiemstra, Hans E Schoemaker, Floris PJT Rutjes, Palladium-Catalyzed Cyclization Reactions of Acetylene-Containing Amino Acids Advanced Synthesis & Catalysis. ,vol. 344, pp. 70- 83 ,(2002) , 10.1002/1615-4169(200201)344:1<70::AID-ADSC70>3.0.CO;2-1
Bartolo Gabriele, Giuseppe Salerno, Mirco Costa, Gian Paolo Chiusoli, Recent developments in the synthesis of heterocyclic derivatives by PdI2-catalyzed oxidative carbonylation reactions Journal of Organometallic Chemistry. ,vol. 687, pp. 219- 228 ,(2003) , 10.1016/S0022-328X(03)00789-7
Ichiya Ninomiya, Recent progress in the synthesis of indole alkaloids Journal of Natural Products. ,vol. 55, pp. 541- 564 ,(1992) , 10.1021/NP50083A001
Alejandro Varela-Fernández, Jesús A. Varela, Carlos Saá, Ruthenium-Catalyzed Cycloisomerization of Aromatic Homo- and Bis-Homopropargylic Amines/Amides: Formation of Indoles, Dihydroisoquinolines and Dihydroquinolines Advanced Synthesis & Catalysis. ,vol. 353, pp. 1933- 1937 ,(2011) , 10.1002/ADSC.201100095
Chinmay Chowdhury, Sanjukta Mukherjee, Biswajit Chakraborty, Basudeb Achari, A rapid and facile method for the general synthesis of 3-aryl substituted 4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyrazines and their ring fused analogues Organic and Biomolecular Chemistry. ,vol. 9, pp. 5856- 5862 ,(2011) , 10.1039/C1OB05255A
Hayato Sakai, Ken Tsutsumi, Tsumoru Morimoto, Kiyomi Kakiuchi, One-Pot/Four-Step/Palladium-Catalyzed Synthesis of Indole Derivatives: The Combination of Heterogeneous and Homogeneous Systems Advanced Synthesis & Catalysis. ,vol. 350, pp. 2498- 2502 ,(2008) , 10.1002/ADSC.200800405
Manfred Eitel, Ulf Pindur, Selective Wittig Reactions for the Synthesis of Variously Substituted 2-Vinylindoles Synthesis. ,vol. 1989, pp. 364- 367 ,(1989) , 10.1055/S-1989-27253
Anna J. Kochanowska-Karamyan, Mark T. Hamann, Marine indole alkaloids: potential new drug leads for the control of depression and anxiety Chemical Reviews. ,vol. 110, pp. 4489- 4497 ,(2010) , 10.1021/CR900211P