Synthesis 2013; 45(21): 3007-3017
DOI: 10.1055/s-0033-1338526
paper
© Georg Thieme Verlag Stuttgart · New York

An Efficient and Mild Synthesis of Tetrahydro-4H-indol-4-one Derivatives via a Domino Reaction in Water

Furen Zhang
School of Chemistry and Chemical Engineering, Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing, Zhejiang Province 312000, P. R. of China   Fax: +86(575)88345862   Email: qichenze@usx.edu.cn
,
Chunmei Li
School of Chemistry and Chemical Engineering, Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing, Zhejiang Province 312000, P. R. of China   Fax: +86(575)88345862   Email: qichenze@usx.edu.cn
,
Chenze Qi*
School of Chemistry and Chemical Engineering, Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing, Zhejiang Province 312000, P. R. of China   Fax: +86(575)88345862   Email: qichenze@usx.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 01 July 2013

Accepted after revision: 12 August 2013

Publication Date:
05 September 2013 (online)


Abstract

An efficient domino approach for the synthesis of tetrahydro-4H-indol-4-one derivatives has been established. The use of catalytic amount of l-proline in water at 60 °C makes it quite simple, more convenient, and environmentally benign.

Supporting Information

 
  • References


    • Selected recent examples:
    • 1a Cariou K, Ronan B, Mignani S, Fensterbank L, Malacria M. Angew. Chem. Int. Ed. 2007; 46: 1881
    • 1b Yin Y, Ma W, Chai Z, Zhao G. J. Org. Chem. 2007; 72: 5731
    • 1c Liu KG, Robicahud AJ, Lo JR, Mattes JF, Cai Y. Org. Lett. 2006; 8: 5769
    • 1d Kaspar LT, Ackermann L. Tetrahedron 2005; 61: 11311
    • 1e Campos KR, Woo JC. S, Lee S, Tillyer RD. Org. Lett. 2004; 6: 79
    • 1f Hong KB, Lee CW, Yum EK. Tetrahedron Lett. 2004; 45: 693
    • 1g Cacchi S, Fabrizi G, Parisi LM. Org. Lett. 2003; 5: 3843
    • 1h Siebeneicher H, Bytschkov I, Doye S. Angew. Chem. Int. Ed. 2003; 42: 3042
    • 1i Onitsuka K, Suzuki S, Takahashi S. Tetrahedron Lett. 2002; 43: 6197
    • 1j Rutherford JF, Rainka MP, Buchwald SL. J. Am. Chem. Soc. 2002; 124: 15168
    • 1k Tokunaga M, Ota M, Haga M, Wakatsuki Y. Tetrahedron Lett. 2001; 42: 3865
    • 1l Verspui G, Elbertse G, Sheldon FA, Hacking MA. P. J, Sheldon RA. Chem. Commun. 2000; 1363
    • 1m Ackermann L. Synlett 2007; 507
    • 1n Humphrey GR, Kuethe JT. Chem. Rev. 2006; 106: 2875
    • 1o Gilchrist TL. J. Chem. Soc., Perkin Trans. 1 2001; 2491
    • 1p Gribble GW. J. Chem. Soc., Perkin Trans. 1 2000; 1045
    • 1q Cacchi S, Fabrizi G. Chem. Rev. 2005; 105: 2873
    • 1r Kuethe JT, Wong A, Davies IW. J. Org. Chem. 2004; 69: 7752
    • 1s Tursky M, Lorentz-Petersen LL. R, Olsen LB, Madsen R. Org. Biomol. Chem. 2010; 8: 5576
    • 1t Fristrup P, Tursky M, Madsen R. Org. Biomol. Chem. 2012; 10: 2569
    • 1u Porcheddu A, Mura MG, De Luca L, Pizzetti M, Taddei M. Org. Lett. 2012; 14: 6112
  • 2 Alex K, Tillack A, Schwarz N, Beller M. Angew. Chem. Int. Ed. 2008; 47: 2304
    • 3a Coleman CM, O’Shea DF. J. Am. Chem. Soc. 2003; 125: 4054
    • 3b Dunetz JR, Danheiser RL. J. Am. Chem. Soc. 2005; 127: 5776
    • 3c Fayol A, Fang Y.-Q, Lautens M. Org. Lett. 2006; 8: 4203
    • 3d Andreev IA, Belov DS, Kurkin AV, Yurovskaya MA. Eur. J. Org. Chem. 2013; 649
  • 4 Cui SL, Wang J, Wang YG. J. Am. Chem. Soc. 2008; 130: 13526
    • 5a Barluenga J, Trincado M, Rubio E, Gonzalez JM. Angew. Chem. Int. Ed. 2003; 42: 2406
    • 5b Barluenga J, Rodriguez F, Fananas FJ. Chem. Asian J. 2009; 4: 1036
    • 5c Bernini R, Fabrizi G, Sferrazza A, Cacchi S. Angew. Chem. Int. Ed. 2009; 48: 8078
    • 5d Jiang B, Yi MS, Shi F, Tu SJ, Pindi S, McDowell P, Li GG. Chem. Commun. 2012; 48: 808
    • 6a Dalko PI, Moisan L. Angew. Chem. Int. Ed. 2004; 43: 5138
    • 6b MacMillan DW. C. Nature (London) 2008; 455: 304
    • 6c Kotsuki H, Ikishima H, Kuyama A. Heterocycles 2008; 75: 757
    • 6d Bertelsen S, Jørgensen KA. Chem. Soc. Rev. 2009; 38: 2178
    • 7a Tanimoro T, Ueno M, Takeda K, Kirihata M, Tanimori S. J. Org. Chem. 2012; 77: 7488
    • 7b Tanimori S, Kobayashi Y, Iesaki Y, Ozaki Y, Kirihata M. Org. Biomol. Chem. 2012; 10: 1381
    • 7c Nezhad AK, Sarikhani S, Shahidzadeh ES, Panahi F. Green Chem. 2012; 14: 2876
    • 7d Rao SN, Mohan DC, Adimurthy S. Org. Lett. 2013; 15: 1496
  • 8 Alcaide B, Almendros P, Luna A, Torres MR. J. Org. Chem. 2006; 71: 4818
    • 9a Janey JM, Hsiao Y, Armstrong III JD. J. Org. Chem. 2006; 71: 390
    • 9b List B, Pojarliev P, Biller WT, Martin HJ. J. Am. Chem. Soc. 2002; 124: 827
    • 10a Hanessian S, Pham V. Org. Lett. 2000; 2: 2975
    • 10b Rasalkar MS, Potdar MK, Mohile SS, Salunkhe MM. J. Mol. Catal. A: Chem. 2005; 235: 267
    • 10c Kotrusz P, Toma S. Molecules 2006; 11: 197
    • 10d Kotrusz P, Toma S. ARKIVOC 2006; (v): 100
  • 11 Ramachary DB, Chowdari NS, Barbas CF. Angew. Chem. Int. Ed. 2003; 42: 4233
  • 12 Bogevig A, Juhl K, Kumaragurubaran N, Zhuang W, Jørgensen KA. Angew. Chem. Int. Ed. 2002; 41: 1790
  • 13 Hossein AO, Elham R, Majid MH. J. Chem. Res. 2006; 246
    • 14a Yadav JS, Kumar SP, Kondaji G, Rao RS, Nagaiah K. Chem. Lett. 2004; 33: 1168
    • 14b Mabry J, Ganem B. Tetrahedron Lett. 2006; 47: 55
    • 15a Indumathi S, Perumal S, Menéndez JC. J. Org. Chem. 2010; 75: 472
    • 15b Wang HY, Li LL, Lin W, Xu P, Huang ZB, Shi DQ. Org. Lett. 2012; 14: 4598
    • 16a Barrett AG. M, Graboski GG. Chem. Rev. 1986; 86: 751
    • 16b Bui T, Syed S, Barbas III CF. J. Am. Chem. Soc. 2009; 131: 8758
    • 17a Ishikawa T, Miyahara T, Asakura M, Higuchi S, Miyaushi Y, Saito S. Org. Lett. 2005; 7: 1211
    • 17b Barange DK, Ragu BR, Kavala V, Kuo CW, Tu YC, Yao CF. Tetrahedron 2011; 66: 3754
    • 18a Miyashita M, Kumazawa T, Yoshikoshi A. J. Org. Chem. 1980; 45: 2945
    • 18b Yanami T, Ballatore A, Miyashita M, Kato M, Yoshikoshi A. J. Chem. Soc., Perkin Trans. 1 1978; 1144
    • 18c Arai M, Miyauchi Y, Miyahara T, Ishikawa T, Saito S. Synlett 2009; 122
    • 19a Tu SJ, Li CM, Li GG, Cao LJ, Shao QQ, Zhou DX, Jiang B, Zhou JF, Xia M. J. Comb. Chem. 2007; 9: 1144
    • 19b Tu SJ, Li CM, Shi F, Zhou DX, Shao QQ, Cao LJ, Jiang B. Synthesis 2008; 369
    • 19c Shi F, Li CM, Xia M, Miao KJ, Zhao YX, Tu SJ, Zheng WF, Zhang G, Ma N. Bioorg. Med. Chem. Lett. 2009; 19: 5565
    • 20a Maiti S, Biswas S, Jana U. J. Org. Chem. 2010; 75: 1674
    • 20b Khan AT, Lal M, Bagdi PR, Basha RS, Saravanan P, Patra S. Tetrahedron Lett. 2012; 53: 4145
    • 20c Reddy GR, Reddy TR, Joseph SC, Reddy KS, Pal M. RSC Adv. 2012; 2: 3387