Triflic acid-promoted cycloisomerization of 2-alkynylphenyl isothiocyanates and isocyanates: a novel synthetic method for a variety of indole derivatives

作者: Takao Saito , Yoshihiko Sonoki , Takashi Otani , Noriki Kutsumura

DOI: 10.1039/C4OB00825A

关键词: Organic chemistryTriflic acidCycloisomerizationChemistryIndole testPhysical and Theoretical ChemistryBiochemistry

摘要: A unique method for synthesis of structurally diverse types of indoles involving a triflic acid-promoted cycloisomerization and a Wagner–Meerwein-type rearrangement is described.

参考文章(81)
Paul Knochel, Gary A. Molander, Comprehensive organic synthesis Elsevier. ,(2014)
Takashi Otani, Takao Saito, Ryota Sakamoto, Hiroyuki Osada, Akihito Hirahara, Naoki Furukawa, Noriki Kutsumura, Tsukasa Matsuo, Kohei Tamao, Intramolecular [2+2+2] cycloaddition of bis(propargylphenyl)carbodiimides: synthesis of L-shaped π-extended compounds with pyrrolo[1,2-a][1,8]naphthyridine corner units Chemical Communications. ,vol. 49, pp. 6206- 6208 ,(2013) , 10.1039/C3CC42792G
Xuhui Ju, Yan Liang, Pingjing Jia, Weifei Li, Wei Yu, Synthesis of oxindoles via visible light photoredox catalysis Organic and Biomolecular Chemistry. ,vol. 10, pp. 498- 501 ,(2012) , 10.1039/C1OB06652H
Morteza Bararjanian, Saeed Balalaie, Frank Rominger, Barahman Movassagh, Hamid Reza Bijanzadeh, Six-component reactions for the stereoselective synthesis of 3-arylidene-2-oxindoles via sequential one-pot Ugi/Heck carbocyclization/Sonogashira/nucleophilic addition. Journal of Organic Chemistry. ,vol. 75, pp. 2806- 2812 ,(2010) , 10.1021/JO902713X
Yan Fang, Chengming Wang, Shengqin Su, Haizhu Yu, Yong Huang, Selective synthesis of indazoles and indoles via triazene–alkyne cyclization switched by different metals Organic and Biomolecular Chemistry. ,vol. 12, pp. 1061- 1071 ,(2014) , 10.1039/C3OB42088D
Takashi Otani, Shinichi Kunimatsu, Hiroshi Nihei, Yuko Abe, Takao Saito, Synthesis of quinoline-2-thiones via tandem indium(III)-promoted Friedel-Crafts alkenylation-cyclization of 2-alkynylphenyl isothiocyanates. Organic Letters. ,vol. 9, pp. 5513- 5516 ,(2007) , 10.1021/OL7024668
Heinz A. Staab, Gerhard Walther, Synthese von Isothiocyanaten European Journal of Organic Chemistry. ,vol. 657, pp. 104- 107 ,(1962) , 10.1002/JLAC.19626570114
Feng Zhou, Yun-Lin Liu, Jian Zhou, Catalytic Asymmetric Synthesis of Oxindoles Bearing a Tetrasubstituted Stereocenter at the C‐3 Position Advanced Synthesis & Catalysis. ,vol. 352, pp. 1381- 1407 ,(2010) , 10.1002/ADSC.201000161