Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 24
393
Views
21
CrossRef citations to date
0
Altmetric
Original Articles

A New Bismuth Nitrate–Catalyzed Electrophilic Substitution of Indoles with Carbonyl Compounds Under Solvent-Free Conditions

, , &
Pages 3678-3682 | Received 26 May 2009, Published online: 09 Nov 2010

REFERENCES

  • Lodyga-Chruscinska , E. ; Turek , M. Compounds containing indole ring—the future of medicine. PharmaChem. 2009, 8(7–8), 6–8.
  • Varma , R. S. Solvent-free organic syntheses . Green Chem. 1999 , 1 , 43 – 55 .
  • (a) Babu , G. ; Sridhar , N. ; Perumal , P. T. A convenient method of synthesis of bis-indolylmethanes: Indium trichloride-catalysed reactions of indole with aldehydes and Schiff's bases . Synth. Commun. 2000 , 30 , 1609 – 1614 ; (b) Nagarajan , R. ; Perumal , P. T. InCl3- and In(OTf)3-catalyzed reactions: Synthesis of 3-acetyl indoles, bis-indolymethane and indolyquinoline derivatives . Tetrahedron 2002 , 58 , 1229 – 1232 ; (c) Mi , X.-L. ; Luo , S.-Z. ; He , J.-Q. ; Cheng , J.-P. Dy(OTf)3 in ionic liquid: An efficient catalytic system for reaction of indole with aldehydes/ketones or mines . Tetrahedron Lett. 2004 , 45 , 4567 – 4570 ; (d) Bandgar , B. P. ; Shaikh , K. A. Organic reactions in aqueous medium: InF3 catalyzed synthesis of bis(indolyl)methanes in water under mild conditions . J. Chem. Res. Synop. 2004 , 34 – 36 ; (e) Chen , D. ; Yu , L. ; Wang , P. G. Lewis acid-catalyzed reactions in protic media. Lanthanide-catalyzed reactions of indoles with aldehydes or ketones . Tetrahedron Lett. 1996 , 37 , 4467 – 4470 ; (f) Kamal , A. ; Qureshi , A. A. Synthesis of substituted di-indolylmethanes in aqueous medium at room temperature . Tetrahedron 1963 , 19 , 513 – 520 ; (g) Yadav , J. S. ; Reddy , B. V. S. ; Murthy , Ch. V. S. R. ; Kumar , G. M. ; Madan , Ch. Lithium perchlorate-catalysed reactions of indoles: An expeditious synthesis of bis(indolyl)methanes . Synthesis 2001 , 783 – 787 ; (h) Lin , X.-F. ; Cui , S.-L. ; Wang , Y.-G. Mild and efficient synthesis of bis-indolylmethanes catalyzed by tetrabutylammonium tribromide . Syn. Commun. 2006 , 36 , 3153 – 3160 ; (i) Mo , L.-P. ; Ma , Z.-C. ; Zhang , Z.-H. CuBr2-catalyzed synthesis of Bis(indolyl)methanes . Synth. Commun. 2005 , 35 , 1997 – 2004 ; (j) Xia , M. ; Wang , S.-B. ; Yuan , W.-B. Lewis acid-catalyzed electrophilic substitution of indoles with aldehydes and Schiff's bases under microwave solvent-free irradiation . Synth. Commun. 2004 , 34 , 3175 – 3182 ; (k) Koshima , H. ; Matsuaka , W. N-Bromosuccinimide-catalyzed condensations of indoles with carbonyl compounds under solvent-free conditions . J. Heterocycl. Chem. 2002 , 39 , 1089 – 1091 ; (l) Nagarajan , R. ; Perumal , P. T. Potassium hydrogen sulfate-catalyzed reactions of indoes: A mild, expedient synthesis of bis-indlymethanes . Chem. Lett. 2004 , 33 , 288 – 289 ; (m) Ramesh , C. ; Baneree , J. ; Pal , R. ; Das , B. Silica-supported sodium hydrogen sulfate and amberlyst-15: Two efficient heterogenos catalysts for facile synthesis of bis- and tris(1H-indol-3-yl)methanes from indoles and carbonyl compounds . Adv. Synth. Catal. 2003 , 345 , 557 – 559 ; (n) Ramesh , C. ; Ravindranath , N. ; Das , B. Electrophilic substitution reactions of indoles with carbonyl compounds using ceric ammonium nitrate: A novel and efficient method for the synthesis of di- and tri-indolylmethanes . J. Chem. Res. Synop. 2003 , 72 – 74 ; (o) Chakrabarty , M. ; Gosh , N. ; Basak , R. ; Harigaya , Y. Dry reaction of indoles with carbonyl compounds on montmorillonite K10 clay: A mild, expedient synthesis of diindolylalkanes and vibrindole A . Tetrahedron Lett. 2002 , 43 , 4075 – 1078 ; (p) Li , W.-J. ; Lin , X.-F. ; Jun , W. ; Li , G.-L. ; Wang , Y.-G. A mild and efficient synthesis of bis-Indolylmethanes catalyzed by sulfamic acid . Synth. Commun. 2005 , 35 , 2765 – 2769 ; (q) Karthik , M. ; Tripathi , A. K. ; Gupta , N. M. ; Palanichamy , M. ; Murugesan , V. Zeolite-catalyzed electrophilic substitution reactions of indoles with aldehydes: Synthesis of bis(indolyl)methanes . Catal. Commun. 2004 , 5 , 371 – 375 ; (r) Zolfigol , M. A. ; Salehi , P. ; Shirl , M. An efficient procedure for the preparation of mono- and di-bis-indolyl methanes catalyzed by molibdatophosphoric acid . Phosphorus, Sulfur Silicon Relat. Elem. 2004 , 179 , 2273 – 2277 ; (s) Sharma , G. V. M. ; Reddy , J. J. ; Lakshmi , P. S. ; Krishna , P. R. A versatile and practical synthesis of bis(indoyl)methanes/bis(indolyl)glycoconjugates catalyzed by trichloro-1,3,5-triazine . Tetrahedron Lett. 2004 , 45 , 7729 – 7732 ; (t) Feng , X.-L. ; Guan , C.-J. ; Zhao , C.-X. Ion exchange resin–catalyzed condensation of indole and carbonyl compounds—synthesis of bis-indolylmethanes . Syn. Commun. 2004 , 34 , 487 – 492 ; (u) Yadav , J. S. ; Reddy , B. V. S. ; Sunitha , S. Efficient and eco-friendly process for the synthesis of bis(1H-indol-3-yl)methanes using ionic liquids . Adv. Synth. Catal. 2003 , 345 , 349 – 352 ; (v) Penieres-Carillo , G. ; Garcia-Estrada , J. G. ; Gutierrez-Ramirez , J. L. ; Alvarez-Toledano , C. Infrared-assisted eco-friendly selective synthesis of diindolylmethanes . Green. Chem. 2003 , 5 , 337 – 339 .
  • (a) Srivastava , N. ; Banik , B. K. Bismuth nitrate-catalyzed versatile michael reactions . J. Org. Chem. 2003 , 68 , 2109 – 2114 ; (b) Srivastava , N. ; Dasgupta , S. K. ; Banik , B. K. A remarkable bismuth nitrate-catalyzed protection of carbonyl compounds . Tetrahedron Lett. 2003 , 44 , 1191 – 1193 ; (c) Banik , B. K. ; Adler , D. ; Nguyen , P. ; Srivastava , N. A new bismuth nitrate-induced stereospecific glycosylation of Alcohols . Heterocycles. 2003 , 61 , 101 – 104 ; (d) Banik , B. K. ; Samajdar , S. ; Banik , I. ; Ng , S. ; Hann , J. Montmorillonite impregnated with bismuth nitrate: Microwave-assisted facile nitration of β-lactams . Heterocycles 2003 , 61 , 97 – 100 .
  • (a) Samajdar , S. ; Becker , F. F. ; Banik , B. K. Surface-mediated highly efficient regioselective nitration of aromatic compounds by bismuth nitrate . Tetrahedron Lett. 2000 , 41 , 8017 – 8020 ; (b) Samajdar , S. ; Becker , F. F. ; Banik , B. K. Montmorillonite impregnated with bismuth nitrate: A versatile reagent for the synthesis of nitro compounds of biological significance . ARKIVOC 2001 , 2 , TG-223G ; (c) Banik , B. K. ; Reddy , A. T. ; Datta , A. ; Mukhopadhyay , C. Microwave-induced bismuth nitrate-catalyzed synthesis of dihydropyrimidones via Biginelli condensation under solventless conditions . Tetrahedron Lett. 2007 , 48 , 7392 – 7394 ; (d) Bose , A. ; Sanjoto , W. P. ; Villarreal , S. ; Aguilar , H. ; Banik , B. K. Novel nitration of estrone by metal nitrates . Tetrahedron Lett. 2007 , 48 , 3945 – 3947 .
  • L. I. and C. A. are undergraduate research participants.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.