BibTex RIS Kaynak Göster

Heteropolyacid Catalyzed Synthesis Of Indole Derivatives Via Fischer Indole Synthesis

Yıl 2011, Cilt: 24 Sayı: 4, 709 - 714, 16.12.2011

Mina Saeedı Akram Fallah Maryam Amrollah Yahya Beheshtıha Fatemeh Bamoharram

Öz

ABSTRACT

Different indole and carbazole derivatives have been synthesized via Fischer indole synthesis in the presence of catalytic amount of H3PW12O40 in methanol

 

Key Words: Fischer indole synthesis, carbazole, indole, Keggin-type heteropolyacids.

 

Anahtar Kelimeler

Fischer indole synthesis carbazole indole Keggin-type heteropolyacids.

Kaynakça

  • [1] Lo, K.K.W., Tsang, K.H.K., Hui, W.K. and Zhu, N., “Luminescent rhenium(I) diimine indole conjugates-photophysical, electrochemical and protein-binding properties”, Chem. Commun., 2704-2705 (2003).
  • [2] Ramirez, A. and Garcia-Rubio, S., “Current progress in the chemistry and pharmacology of akuammiline alkaloids”, Curr. Med. Chem., 10: 1891-1915 (2003).
  • [3] Gribble, G.W., “Recent developments in indole ring synthesis-methodology and applications”, J. Chem. Soc., Perkin Trans. 1, 1045-1075 (2000).
  • [4] Jarak, I., Kralj, M., Piantanida, I., Suman, L., Zinic, M., Pavelic, K., Karminiski- Zamola, G., “Novel cyano- and amidino-substituted derivatives of thieno[2,3-b]- and thieno[3,2- b]thiophene-2-carboxanilides and thieno[3′,2′:4,5]thieno- and thieno[2′,3′:4,5]thieno [2,3-c]quinolones: Synthesis, photochemical synthesis, DNA binding, and antitumor evaluation”, Bioorg. Med. Chem., 14: 2859-2868 (2006).
  • [5] Heinrich, T. and Bottcher, H., “A new synthesis of indole 5-carboxylic acids and 6-hydroxyindole-5-carboxylic acids in the preparation of an o-hydroxylated metabolite of vilazodone”, Bioorg. Med. Chem. Lett., 14: 2681-2684 (2004).
  • [6] Veluri, R., Oka, I., Do¨bler, I.W. and Laatsch, H., “New indole alkaloids from the north sea bacterium vibrio parahaemolyticus Bio249”, J. Nat. Prod. 66: 1520-1523 (2003).
  • [7] Bergman, J. and Tilstam, U., “Structure determination of candidine, a violet indolic constituent from culture solutions of Candida lipolytica”, Tetrahedron, 41: 2883-2884 (1985).
  • [8] Dusman, L.T., Jorge, T.C.M., Souza, M.C.D., Eberlin, M.N., Meurer, E.C., Bocca, C.C., Basso, E.A. and Sarragiotto, M. H., “Monoterpene indole alkaloids from Palicourea crocea”, J. Nat. Prod., 67: 1886-1888 (2004).
  • [9] (a) Humphrey, G.R. and Kuethe, J.T., “Practical methodologies for the synthesis of indoles”, Chem. Rev., 106: 2875-2911(2006); (b) Dalpozzo, R. and Bartoli, G., “Bartoli indole synthesis”, Curr. Org. Chem., 9: 163-178 (2005).
  • [10] Robinson, B. “Studies on the Fischer indole synthesis”, Chem. Rev., 69: 227-250 (1969).
  • [11] (a) Sudhakara, A., Jayadevappa, H., Mahadevan, K.M. and Hulikal, V., “Efficient Synthesis of 2- Ethoxycarbonyl Indoles”, Synth. Commun., 39: 2506-2515(2009); (b) Dhakshinamoorthy, A. and Pitchumani, K., “Facile clay-induced Fischer indole synthesis: A new approach to synthesis of 1,2,3,4-tetrahydrocarbazole and indoles”, Appl. Catal., A, 292: 305-311(2005); (c) Park, I.K., Suh, S.E., Lim, B.Y. and Cho, C.G., “Aryl hydrazide beyond as surrogate of aryl hydrazine in the Fischer indolization: the synthesis of NCbz-indoles, N-Cbz-carbazoles, and N,N′-BisCbz-pyrrolo[2,3-f]indoles”, Org. Lett., 11: 5454- 5456 (2009); (d) Jeanty, M., Blu, J., Suzenet, F.
  • and Guillaumet, G., “Synthesis of 4- and 6- azaindoles via the Fischer reaction”, Org. Lett., 11: 5142-5145(2009); (e) Srinivasa, A., Mahadevan, K.M., Varma, P.P., Sudhakara, A. “Antimony (III) sulfate catalyzed one-pot synthesis of 2,3-disubstitutedindoles”, Phosphorus, Sulfur Silicon Relat. Elem., 184: 1843-1853 (2009); (f) Wache, N. and Christoffers, J., “Synthesis of some new optically active octahydro-6H-pyrido[4,3-b]-carbazole derivatives” Synlett, 3016-3018 (2009); (g) Sudhakara, A., Jayadevappa, H., Kumar, H.N.H. and Mahadevan, K.M., “Bismuth nitrate promoted Fischer indole synthesis: A simple and convenient approach for the synthesis of alkyl indoles”, Lett. Org. Chem., 6: 159-164 (2009); (h) Zhong, L. and Chuah, G.K., “Fischer indole synthesis over hydrous zirconia-supported niobium oxide”, Aust. J. Chem., 62: 1027-1033 (2009); (i) Varma, P.P., Sherigara, B.S., Mahadevan, K.M. and Hulikal, V., “Efficient and straightforward synthesis of tetrahydrocarbazoles and 2,3-dimethyl indoles catalyzed by CAN”, Synth. Commun., 39: 158-165 (2009); (j) Deorha, D.S. and Joshi, S.S., “Cyclic products from hydrazines. I. nitroindoles, nitrotetrahydrocarbazoles, nitroindolenines, and nitrotetrahydrocarhazolenines”, J. Org. Chem., 26: 3527-3530 (1961).
  • [12] Kozhevnikov, I.V., “Catalysis by heteropoly acids and multicomponent polyoxometalates in liquidphase reactions”, Chem. Rev., 98: 171-198 (1998).
  • [13] (a) Heravi, M.M., Derikvand, F. and Bamoharram, F.F., “A catalytic method for synthesis of Biginelli-type 3,4-dihydropyrimidin- 2(1H)-one using 12-tungstophosphoric acid”, J. Mol. Catal. A: Chem., 242: 173-175 (2005); (b) Heravi, M.M., Zadsirjan, V., Bakhtiari, K., Oskooie, H.A. and Bamoharram, F.F., “Green and reusable heteropolyacid catalyzed oxidation of benzylic, allylic and aliphatic alcohols to carbonyl compounds”, Catal. Commun., 8: 315-318 (2007); (c) Heravi, M.M., Derikvand, F., Haeri, A., Oskooie, H.A. and Bamoharram, F.F., “Heteropolyacids as green and reusable catalysts for the synthesis of isoxazole derivatives”, Synth. Commun., 8: 135-140 (2008); (d) Heravi, M.M., Sadjadi, S., Oskooie, H.A., Shoar, R.H. and Bamoharram, F.F., “Heteropolyacids as heterogeneous and recyclable catalysts for the synthesis of benzimidazoles”, Catal. Commun., 9: 504-507 (2008); (e) Heravi, M.M., Sadjadi, S., Shoar, R.H., Oskooie, H.A. and Bamoharram, F.F., “Heteropolyacids as green and reusable catalysts for the synthesis of 3,1,5- benzoxadiazepines”, Molecules, 12: 255-262 (2007); (f) Heravi, M.M., Sadjadi, S., Oskooie, H.A., Shoar, R.H. and Bamoharram, F.F., “The synthesis of coumarin-3-carboxylic acids and 3- acetyl-coumarin derivatives using heteropolyacids as heterogeneous and recyclable catalysts”, Catal. Commun., 9: 470-474 (2008).
  • [14] (a) Heravi, M.M., Sadjadi, S., Haj, N.M., Oskooie, H.A. and Shoar, R.H., “A novel multicomponent synthesis of 4- arylaminoquinazolines”, Tetrahedron Lett., 50: 943-945 (2009); (b) Heravi, M.M., Baghernejad, B. and Oskooie, H.A., “A novel three-component reaction for the synthesis of N-cyclohexyl-3-arylquinoxaline-2-amines”, Tetrahedron Lett., 50: 767-769 (2009); (c) Heravi, M.M., Baghernejad, B., Oskooie, H.A. and Shoar, R.H., “A novel and facile synthesis of 2-(cyclohexylamino)-6,7- dihydro-3-aryl-1Hindole-4(5H)-ones via a onepot multi-component reaction”, Tetrahedron Lett., 49: 6101-6103 (2008).
  • [15] (a) Morales, R.C., Tambyrajah, V., Jenkins, P.R., Davies, D.L. and Abbott, A.P., “The regiospecific Fischer indole reaction in choline chloride·2ZnCl2 with product isolation by direct sublimation from the ionic liquid”, Chem. Commun., 158-159 (2004); (b) Campaigne, E. and Lake, R.D., “Synthesis of tetrahydrocarbazoles and carbazoles by the Bischler reaction”, J. Org. Chem., 24: 478- 487 (1959); (c) Scott, T.L., Burke, N., CarreroMartínez, G. and SÖderberg, B.C.G., “Synthesis of 1,2,3,4-tetrahydrocarbazoles and related tricyclic indoles” Tetrahedron, 63: 1183-1190 (2007); (d) Saha, B.P. and Menezes, A., “A new route to the synthesis of new 5,7-dinitro-2- phenylindole and its derivatives” Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 34: 535-536 (1995); (e) Kuehne, M.E. and Kitagawa, T., “Reactions of indoles with benzyne” J. Org. Chem., 29: 1270-1273 (1964); (f) Cho, C.S., Kim, j.H., Kim, T.-J. and Shim, S.C., “Ruthenium-catalyzed heteroannulation of anilines with alkanolammonium chlorides leading to indoles”, Tetrahedron, 57: 3321-3329 (2001); (g) Saleha, S., Siddiqui, A.A. and Khan, N.H., “A convenient synthesis of new indole derivatives”, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 19: 81-82 (1980); (h) Hamel, P., Zajac, N., Atkinson, J.G. and Girard, Y., “Nonreductive desulfenylation of 3-indolyl sulfides. Improved syntheses of 2-substituted indoles and 2-indolyl sulfides”, J. Org. Chem., 59: 6372-6377 (1994); (i) Bratulescu, G., “A new and efficient one-pot synthesis of indoles” Tetrahedron Lett., 49: 984- 986 (2008)

Yıl 2011, Cilt: 24 Sayı: 4, 709 - 714, 16.12.2011

Mina Saeedı Akram Fallah Maryam Amrollah Yahya Beheshtıha Fatemeh Bamoharram

Öz

Kaynakça

  • [1] Lo, K.K.W., Tsang, K.H.K., Hui, W.K. and Zhu, N., “Luminescent rhenium(I) diimine indole conjugates-photophysical, electrochemical and protein-binding properties”, Chem. Commun., 2704-2705 (2003).
  • [2] Ramirez, A. and Garcia-Rubio, S., “Current progress in the chemistry and pharmacology of akuammiline alkaloids”, Curr. Med. Chem., 10: 1891-1915 (2003).
  • [3] Gribble, G.W., “Recent developments in indole ring synthesis-methodology and applications”, J. Chem. Soc., Perkin Trans. 1, 1045-1075 (2000).
  • [4] Jarak, I., Kralj, M., Piantanida, I., Suman, L., Zinic, M., Pavelic, K., Karminiski- Zamola, G., “Novel cyano- and amidino-substituted derivatives of thieno[2,3-b]- and thieno[3,2- b]thiophene-2-carboxanilides and thieno[3′,2′:4,5]thieno- and thieno[2′,3′:4,5]thieno [2,3-c]quinolones: Synthesis, photochemical synthesis, DNA binding, and antitumor evaluation”, Bioorg. Med. Chem., 14: 2859-2868 (2006).
  • [5] Heinrich, T. and Bottcher, H., “A new synthesis of indole 5-carboxylic acids and 6-hydroxyindole-5-carboxylic acids in the preparation of an o-hydroxylated metabolite of vilazodone”, Bioorg. Med. Chem. Lett., 14: 2681-2684 (2004).
  • [6] Veluri, R., Oka, I., Do¨bler, I.W. and Laatsch, H., “New indole alkaloids from the north sea bacterium vibrio parahaemolyticus Bio249”, J. Nat. Prod. 66: 1520-1523 (2003).
  • [7] Bergman, J. and Tilstam, U., “Structure determination of candidine, a violet indolic constituent from culture solutions of Candida lipolytica”, Tetrahedron, 41: 2883-2884 (1985).
  • [8] Dusman, L.T., Jorge, T.C.M., Souza, M.C.D., Eberlin, M.N., Meurer, E.C., Bocca, C.C., Basso, E.A. and Sarragiotto, M. H., “Monoterpene indole alkaloids from Palicourea crocea”, J. Nat. Prod., 67: 1886-1888 (2004).
  • [9] (a) Humphrey, G.R. and Kuethe, J.T., “Practical methodologies for the synthesis of indoles”, Chem. Rev., 106: 2875-2911(2006); (b) Dalpozzo, R. and Bartoli, G., “Bartoli indole synthesis”, Curr. Org. Chem., 9: 163-178 (2005).
  • [10] Robinson, B. “Studies on the Fischer indole synthesis”, Chem. Rev., 69: 227-250 (1969).
  • [11] (a) Sudhakara, A., Jayadevappa, H., Mahadevan, K.M. and Hulikal, V., “Efficient Synthesis of 2- Ethoxycarbonyl Indoles”, Synth. Commun., 39: 2506-2515(2009); (b) Dhakshinamoorthy, A. and Pitchumani, K., “Facile clay-induced Fischer indole synthesis: A new approach to synthesis of 1,2,3,4-tetrahydrocarbazole and indoles”, Appl. Catal., A, 292: 305-311(2005); (c) Park, I.K., Suh, S.E., Lim, B.Y. and Cho, C.G., “Aryl hydrazide beyond as surrogate of aryl hydrazine in the Fischer indolization: the synthesis of NCbz-indoles, N-Cbz-carbazoles, and N,N′-BisCbz-pyrrolo[2,3-f]indoles”, Org. Lett., 11: 5454- 5456 (2009); (d) Jeanty, M., Blu, J., Suzenet, F.
  • and Guillaumet, G., “Synthesis of 4- and 6- azaindoles via the Fischer reaction”, Org. Lett., 11: 5142-5145(2009); (e) Srinivasa, A., Mahadevan, K.M., Varma, P.P., Sudhakara, A. “Antimony (III) sulfate catalyzed one-pot synthesis of 2,3-disubstitutedindoles”, Phosphorus, Sulfur Silicon Relat. Elem., 184: 1843-1853 (2009); (f) Wache, N. and Christoffers, J., “Synthesis of some new optically active octahydro-6H-pyrido[4,3-b]-carbazole derivatives” Synlett, 3016-3018 (2009); (g) Sudhakara, A., Jayadevappa, H., Kumar, H.N.H. and Mahadevan, K.M., “Bismuth nitrate promoted Fischer indole synthesis: A simple and convenient approach for the synthesis of alkyl indoles”, Lett. Org. Chem., 6: 159-164 (2009); (h) Zhong, L. and Chuah, G.K., “Fischer indole synthesis over hydrous zirconia-supported niobium oxide”, Aust. J. Chem., 62: 1027-1033 (2009); (i) Varma, P.P., Sherigara, B.S., Mahadevan, K.M. and Hulikal, V., “Efficient and straightforward synthesis of tetrahydrocarbazoles and 2,3-dimethyl indoles catalyzed by CAN”, Synth. Commun., 39: 158-165 (2009); (j) Deorha, D.S. and Joshi, S.S., “Cyclic products from hydrazines. I. nitroindoles, nitrotetrahydrocarbazoles, nitroindolenines, and nitrotetrahydrocarhazolenines”, J. Org. Chem., 26: 3527-3530 (1961).
  • [12] Kozhevnikov, I.V., “Catalysis by heteropoly acids and multicomponent polyoxometalates in liquidphase reactions”, Chem. Rev., 98: 171-198 (1998).
  • [13] (a) Heravi, M.M., Derikvand, F. and Bamoharram, F.F., “A catalytic method for synthesis of Biginelli-type 3,4-dihydropyrimidin- 2(1H)-one using 12-tungstophosphoric acid”, J. Mol. Catal. A: Chem., 242: 173-175 (2005); (b) Heravi, M.M., Zadsirjan, V., Bakhtiari, K., Oskooie, H.A. and Bamoharram, F.F., “Green and reusable heteropolyacid catalyzed oxidation of benzylic, allylic and aliphatic alcohols to carbonyl compounds”, Catal. Commun., 8: 315-318 (2007); (c) Heravi, M.M., Derikvand, F., Haeri, A., Oskooie, H.A. and Bamoharram, F.F., “Heteropolyacids as green and reusable catalysts for the synthesis of isoxazole derivatives”, Synth. Commun., 8: 135-140 (2008); (d) Heravi, M.M., Sadjadi, S., Oskooie, H.A., Shoar, R.H. and Bamoharram, F.F., “Heteropolyacids as heterogeneous and recyclable catalysts for the synthesis of benzimidazoles”, Catal. Commun., 9: 504-507 (2008); (e) Heravi, M.M., Sadjadi, S., Shoar, R.H., Oskooie, H.A. and Bamoharram, F.F., “Heteropolyacids as green and reusable catalysts for the synthesis of 3,1,5- benzoxadiazepines”, Molecules, 12: 255-262 (2007); (f) Heravi, M.M., Sadjadi, S., Oskooie, H.A., Shoar, R.H. and Bamoharram, F.F., “The synthesis of coumarin-3-carboxylic acids and 3- acetyl-coumarin derivatives using heteropolyacids as heterogeneous and recyclable catalysts”, Catal. Commun., 9: 470-474 (2008).
  • [14] (a) Heravi, M.M., Sadjadi, S., Haj, N.M., Oskooie, H.A. and Shoar, R.H., “A novel multicomponent synthesis of 4- arylaminoquinazolines”, Tetrahedron Lett., 50: 943-945 (2009); (b) Heravi, M.M., Baghernejad, B. and Oskooie, H.A., “A novel three-component reaction for the synthesis of N-cyclohexyl-3-arylquinoxaline-2-amines”, Tetrahedron Lett., 50: 767-769 (2009); (c) Heravi, M.M., Baghernejad, B., Oskooie, H.A. and Shoar, R.H., “A novel and facile synthesis of 2-(cyclohexylamino)-6,7- dihydro-3-aryl-1Hindole-4(5H)-ones via a onepot multi-component reaction”, Tetrahedron Lett., 49: 6101-6103 (2008).
  • [15] (a) Morales, R.C., Tambyrajah, V., Jenkins, P.R., Davies, D.L. and Abbott, A.P., “The regiospecific Fischer indole reaction in choline chloride·2ZnCl2 with product isolation by direct sublimation from the ionic liquid”, Chem. Commun., 158-159 (2004); (b) Campaigne, E. and Lake, R.D., “Synthesis of tetrahydrocarbazoles and carbazoles by the Bischler reaction”, J. Org. Chem., 24: 478- 487 (1959); (c) Scott, T.L., Burke, N., CarreroMartínez, G. and SÖderberg, B.C.G., “Synthesis of 1,2,3,4-tetrahydrocarbazoles and related tricyclic indoles” Tetrahedron, 63: 1183-1190 (2007); (d) Saha, B.P. and Menezes, A., “A new route to the synthesis of new 5,7-dinitro-2- phenylindole and its derivatives” Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 34: 535-536 (1995); (e) Kuehne, M.E. and Kitagawa, T., “Reactions of indoles with benzyne” J. Org. Chem., 29: 1270-1273 (1964); (f) Cho, C.S., Kim, j.H., Kim, T.-J. and Shim, S.C., “Ruthenium-catalyzed heteroannulation of anilines with alkanolammonium chlorides leading to indoles”, Tetrahedron, 57: 3321-3329 (2001); (g) Saleha, S., Siddiqui, A.A. and Khan, N.H., “A convenient synthesis of new indole derivatives”, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 19: 81-82 (1980); (h) Hamel, P., Zajac, N., Atkinson, J.G. and Girard, Y., “Nonreductive desulfenylation of 3-indolyl sulfides. Improved syntheses of 2-substituted indoles and 2-indolyl sulfides”, J. Org. Chem., 59: 6372-6377 (1994); (i) Bratulescu, G., “A new and efficient one-pot synthesis of indoles” Tetrahedron Lett., 49: 984- 986 (2008)
Toplam 16 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Bölüm Chemistry
Yazarlar

Mina Saeedı

Akram Fallah Bu kişi benim

Maryam Amrollah Bu kişi benim

Yahya Beheshtıha Bu kişi benim

Fatemeh Bamoharram Bu kişi benim

Yayımlanma Tarihi 16 Aralık 2011
Yayımlandığı Sayı Yıl 2011 Cilt: 24 Sayı: 4

Kaynak Göster

APA Saeedı, M., Fallah, A., Amrollah, M., Beheshtıha, Y., vd. (2011). Heteropolyacid Catalyzed Synthesis Of Indole Derivatives Via Fischer Indole Synthesis. Gazi University Journal of Science, 24(4), 709-714.
AMA Saeedı M, Fallah A, Amrollah M, Beheshtıha Y, Bamoharram F. Heteropolyacid Catalyzed Synthesis Of Indole Derivatives Via Fischer Indole Synthesis. Gazi University Journal of Science. Aralık 2011;24(4):709-714.
Chicago Saeedı, Mina, Akram Fallah, Maryam Amrollah, Yahya Beheshtıha, ve Fatemeh Bamoharram. “Heteropolyacid Catalyzed Synthesis Of Indole Derivatives Via Fischer Indole Synthesis”. Gazi University Journal of Science 24, sy. 4 (Aralık 2011): 709-14.
EndNote Saeedı M, Fallah A, Amrollah M, Beheshtıha Y, Bamoharram F (01 Aralık 2011) Heteropolyacid Catalyzed Synthesis Of Indole Derivatives Via Fischer Indole Synthesis. Gazi University Journal of Science 24 4 709–714.
IEEE M. Saeedı, A. Fallah, M. Amrollah, Y. Beheshtıha, ve F. Bamoharram, “Heteropolyacid Catalyzed Synthesis Of Indole Derivatives Via Fischer Indole Synthesis”, Gazi University Journal of Science, c. 24, sy. 4, ss. 709–714, 2011.
ISNAD Saeedı, Mina vd. “Heteropolyacid Catalyzed Synthesis Of Indole Derivatives Via Fischer Indole Synthesis”. Gazi University Journal of Science 24/4 (Aralık 2011), 709-714.
JAMA Saeedı M, Fallah A, Amrollah M, Beheshtıha Y, Bamoharram F. Heteropolyacid Catalyzed Synthesis Of Indole Derivatives Via Fischer Indole Synthesis. Gazi University Journal of Science. 2011;24:709–714.
MLA Saeedı, Mina vd. “Heteropolyacid Catalyzed Synthesis Of Indole Derivatives Via Fischer Indole Synthesis”. Gazi University Journal of Science, c. 24, sy. 4, 2011, ss. 709-14.
Vancouver Saeedı M, Fallah A, Amrollah M, Beheshtıha Y, Bamoharram F. Heteropolyacid Catalyzed Synthesis Of Indole Derivatives Via Fischer Indole Synthesis. Gazi University Journal of Science. 2011;24(4):709-14.