Skip to main content
SpringerLink
Log in

An efficient catalytic reductive amination: A facile one-pot access to 1,2-dihydropyrrolo[3,4-b]indol-3(4H)-ones by using B(C 6 F 5 ) 3 /NaBH 4

  • Published:
Journal of Chemical Sciences Aims and scope Submit manuscript

Abstract

An efficient combination of B(C6F5)3 and NaBH4 was developed for direct reductive amination of aldehydes. A wide range of functional groups such as ester, nitro, nitrile, halogen, alkene, heterocycles were tolerated. Also, acid sensitive protecting groups like TBDMS and TBDPS were not affected. In addition, the present methodology was extended for tandem amination-amidation of 3-formyl-indole-2-carboxylic acids with substituted anilines to afford 1,2-dihydropyrrolo[3,4-b]indol-3(4H)-ones.

An efficient combination of B(C6F5)3 and NaBH4 was developed for direct reductive amination of aldehydes. In addition, B(C6F5)3 catalyzed tandem amination–amidation of 3-formyl-indole-2-carboxylic acids with different substituted anilines to afford substituted 1,2-dihydropyrrolo[3,4-b]indol-3(4H)-ones.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Figure 1
Figure 2
Scheme 1

Similar content being viewed by others

References

  1. Gomez S, Peters F A and Maschmeyer T 2002 Adv. Synth. Catal. 344 1037

  2. Cho B T and Kang S K 2005 Tetrahedron 61 5725

  3. (a) Uday Kumar N, Sudhakar Reddy B, Prabhakar Reddy V and Bandichhor R 2012 Tetrahedron Lett. 53 4354; (b) Tarasevich V A and Kozlov N G 1999 Russ. Chem. Rev. 68 55

  4. (a) Hiroi R, Miyoshi N and Wada M 2002 Chem. Lett. 31 274; (b) Suwa T, Shibata I, Nishino K and Baba A 1999 Org. Lett. 1 1579; (c) Shibata I, Moriuchi-Kawakami T, Tanizawa D, Suwa T, Sugiyama E, Matsuda H and Baba A 1998 J. Org. Chem. 63 383

  5. (a) Nose A and Kudo T 1986 Chem. Pharm. Bull. 34 4817; (b) Reddy S P, Kanjilal S, Sunitha S and Prasad B N R 2007 Tetrahedron Lett. 48 8807; (c) Abdel-Magid A F, Carson K G, Haris B D, Maryanoff C A and Shah R D 1996 J. Org. Chem. 613849; (d) Lai R-Y, Lee C-I and Liu S-T 2008 Tetrahedron 64 1213; (e) Ramachandran V P, Gagare D P, Sakavuyi K and Clark P 2010 Tetrahedron Lett. 51 3167

  6. (a) Chandrasekhar S, Reddy C R and Ahmed M 2000 Synlett 1655; (b) Chandrasekhar S, Reddy M V and Chandraiah L 1999 Synth. Commun. 29 3981; (c) Kumar V, Sharma S, Sharma U, Singh B and Kumar N 2012 Green Chem. 14 3410; (d) Kotsuki H, Yoshimura N, Kadota I, Ushio Y and Ochi M 1990 Synthesis 401; (e) Bhattacharyya S, Chatterjee A and Williamson J S 1997 Synth. Commun. 27 4265

  7. (a) Ranu B C, Majee A and Sarkar A 1998 J. Org. Chem. 63 370; (b) Miccović I V, Ivanović M D, Piatak D M and Bojić V D 1991 Synthesis 11 1043; (c) Itsuno S, Sakurai Y and Ito K 1988 Synthesis 995

  8. (a) Salmi C, Letourneux Y and Brunel J M 2006 Lett. Org. Chem. 3 396; (b) Verardo G, Giumanini A G, Strazzolini P and Poiana M 1993 Synthesis 121; (c) Varma R S and Dahiya R 1998 Tetrahedron 54 6293

  9. (a) Gutierrez C D, Bavetsias V and McDonald E 2005 Tetrahedron Lett. 46 3595; (b) Cabral S, Hulin B and Kawai M 2007 Tetrahedron Lett. 48 7134; (c) Heydari A, Khaksar S, Akbari J, Esfandyari M, Pourayoubi M and Tajbakhsh M 2007 Tetrahedron Lett. 48 1135; (d) Akbar H, Afsaneh A and Maryam E 2007 J. Mol. Catal. A-Chem. 274 169

  10. (a) Periasamy M, Devasagayaraj A, Satyanarayana N and Narayana C 1989 Synth. Commun. 19 565; (b) Bomann M D, Guch I C and DiMare M 1995 J. Org. Chem. 60 5995; (c) Pelter A, Rosser R M and Mills S 1984 J. Chem. Soc., Perkin Trans. 1 717; (d) Sato S, Sakamoto T, Miyazawa E and Kikugawa Y 2004 Tetrahedron 60 7899

  11. (a) Chen B-C, Sundeen J E, Guo P, Bednarz M S and Zhao R 2001 Tetrahedron Lett. 42 1245; (b) Lopez R M and Fu G C 1997 Tetrahedron 53 16349; (c) Apodaca R and Xiao W 2001 Org. Lett. 3 1745; (d) Suwa T, Sugiyama E, Shibata I and Baba A 2000 Synthesis 789

  12. (a) Patel J P, Li A-H, Dong H, Korlipara V L and Mulvihill M J 2009 Tetrahedron Lett. 50 5975; (b) Heydari A, Khaksar S, Esfandyari M and Tajbakhsh M 2007 Tetrahedron 63 3363; (c) Bhanushali J M, Nandurkar S N, Bhor D M and Bhanage B M 2007 Tetrahedron Lett. 48 1273; (d) Chase P A, Welch G C, Jurca T and Stephan D W 2007 Angew. Chem. Int. Ed. 46 8050

  13. (a) Prajapti S K, Nagarsenkar A and Bathini B N 2014 Tetrahedron Lett. 55 1784; (b) Prajapti S K, Nagarsenkar A, Bathini B N 2014 Tetrahedron Lett. 55 3507; (c) Kempf D J, Rosenberg S H, Plattner J J, Shan H L and De B 1991 U.S. Patent 4994477; (d) Zinnes H and Lindo N A 1979 U.S. Patent 4153711

  14. (a) Owellen R J, Fitzgerald J A, Fitzgerald B M, Welsh D A, Walker D M and Southwick P L 1967 Tetrahedron Lett. 18 1741; (b) Kempf D J and Condon S L 1990 J. Org. Chem. 55 1390; (c) Font M, Monge A, Cuartero A, Ellorriaga A, Martinez-Irujo J J, Alberdi E, Santiago E, Prieto I, Lasarte J J Sarobe P and Borrás F 1995 Eur. J. Med. Chem. 30 963; (d) Giovanninetti G, Garuti L, Cavrini V, Gatti R, Mannini Palenzona A and Baserga M 1981 Farmaco Sci. 36 386

  15. (a) Zhang M, Yang H, Zhang Y, Zhu C, Li W, Cheng Y and Hu H 2011 Chem. Comm. 47 6605; (b) Del Pozo C, Corma A, Iglesias M and Sanchez F 2012 J. Catal. 291 110; (c) Bhor M D, Bhanushali M J, Nandurkar N S and Bhanage B M 2008 Tetrahedron Lett. 49 965; (d) Talukdar S and Banerji A 1996 Synth. Commun. 26 1051; (e) Alinezhad H, Tajbakhsh M and Hamidi N 2010 Turk. J. Chem. 34 307; (f) Yamashita M, Kadokura M and Suemitsu R 1984 Bull. Chem. Soc. Jpn. 57 3359; (g) Song H, Yang J, Chen W and Qin Y 2006 Org. Lett. 8 6011; (h) Smith C R and Rajanbabu T V 2008 Org. Lett. 10 1657; (i) Southwick P L and Owellen R J 1960 J. Org. Chem. 25 1133

Download references

Acknowledgements

We thank the Department of Pharmaceuticals (Ministry of Chemicals and Fertilizers) for providing funds and also CSIR-Indian Institute of Chemical Technology, Hyderabad for providing the facilities.

Author information

Authors and Affiliations

  1. Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, Balanagar, Hyderabad, 500037, India

    ATULYA NAGARSENKAR, SANTOSH KUMAR PRAJAPTI & BATHINI NAGENDRA BABU

Authors
  1. ATULYA NAGARSENKAR
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. SANTOSH KUMAR PRAJAPTI
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. BATHINI NAGENDRA BABU
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to BATHINI NAGENDRA BABU.

Additional information

Supporting Information

Spectral data (1H and 13C) are available as part of the supporting information at www.ias.ac.in/chemsci.

Electronic supplementary material

Below is the link to the electronic supplementary material.

(DOC 1.28 MB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

NAGARSENKAR, A., PRAJAPTI, S.K. & BABU, B.N. An efficient catalytic reductive amination: A facile one-pot access to 1,2-dihydropyrrolo[3,4-b]indol-3(4H)-ones by using B(C 6 F 5 ) 3 /NaBH 4 . J Chem Sci 127, 711–716 (2015). https://doi.org/10.1007/s12039-015-0825-y

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12039-015-0825-y

Keywords

Search

Navigation