BibTex RIS Kaynak Göster

Synthesis of Trisubstituted Imidazoles Using Lewis and Bronsted Acid Catalysts

Yıl 2012, Cilt: 25 Sayı: 1, 29 - 34, 24.01.2012

Rahim Hekmatshoar , Rahim Hekmatshoar , Hajar Jahanbakhshı Farnoosh Mousavızadeh Reyhane Rahnamafar

Öz

An efficient and one-pot method for the preparation of trisubstituted imidazoles by condensation of benzil, different aldehydes and ammonium acetate in the presence of  a catalytic amount of NiSO4.7H2O or H3BO3 under different conditions is reported.

 

 

 

                Key Words: Trisubstituted imidazoles, Multi-component

                                     reactions, NiSO4.7H2O, H3BO3, one-pot

                                    reactions,  solid acid catalysts.

 

Anahtar Kelimeler

Trisubstituted imidazoles Multi-component reactions NiSO4.7H2O H3BO3 one-pot reactions solid acid catalysts.

Kaynakça

  • Zhu, J., Bienayme, Wiley-VCH,
  • Weinheim.Germany, Reactions”, (2005)
  • Orru, R.V.A., De Greef, M., “Recent advances in solution-phase multicomponent methodology for the synthesis of heterocyclic compounds”, Synthesis, 1471-1499, (2003).
  • Dembitsky, V.M., Gloriozova, T.A., Poroikov, V. V., “Novel antitumor agents: Marine sponge alkaloids, their synthetic analogs and derivatives”, Mini-rev. Med. Chem, 5: 319-336, (2005).
  • Nagawade, R.R., Shinde, D.B., “Zirconyl chloride- catalyzed multicomponent reaction of naphtoles: An expeditions synthesis of amido alkyl naphtols ”, Acta Chim Sslov, 54: 642-646, (2007).
  • Vallee, B.L., Auld, D.S., “Zinc coordination, function, and structure of zinc enzymes and other proteins”, Biochemistry, 29:5647-5659, (1990).
  • Liu, J., Zhao, Y., Zhou, Y., Li, L., Zhang, T.Y., Zhang, H.,“ Imidazolylidene carbene ligated palladium catalysis of the Heck reaction in the presence of air”, Org. Biomol. Chem., 1:3227-3231, (2003).
  • Grimmett, M.R., Katritzky, A.R. ,Ress, C. W., Scriven, E.F.V., “Comprehensive Heterocyclic Chemistry II” ,Pergamon Press , Oxford(eds), 3: 77-220, (1996).
  • Murry, J. A.,“ Synthetic methodology utilized to prepare substituted imidazole P38 MAP kinase inhibitors”, Curr. Opin. Drug Discovery Dev, 6: 945-965, (2003).
  • Narayana Murthy, S., Madhav, B., Nageswar, Y.V.D., “DABCO as a mild and efficient catalyst system for the synthesis of highly substituted imidazoles strategy”, Tetrahedron Letters, 51: 5252-5257, (2010). condensation
  • Schubert, H., Stodolka, H. J., “Diimidazole.II. Synthesis uberbruckten N,N´-Diimidazolen”, Prakt. Chem., 22: 130-139, (1963). und aromatisch
  • Tsuji, J., Sakai, K., Nemoto, H., Nagashima, H., “Iron and copper catalyzed reaction of benzylamine with carbon tetrachloride: Facile formation of 2,4,5- Triphenylimidazoline deravatives.” , J. Mol. Cata.l, 18: 169-176, (1983).
  • Frantz, E.D., Morency, L., Soheili, A., Murry, J. A., Grabowski, E. J. J., Tillyer, R.D., “Synthesis of substituted Imidazoles via organocatalysis”, Org. Lett., 6: 843-846, (2004).
  • Japp, F.R., Robinson, H.H., “ Constitution des lophins und des amarins”, Ber, 15: 1268-1270, (1882).
  • Wasserman, H.H., Long, Y. O., Zhang, R., Parr, J., “Alkenyl tricarbonyl derivatives of α-amino acids as trielectrophiles. substituted productes”, Tetrahedron Lett, 43: 3351- 3353, (2002). of heterocyclic
  • Liu, J., Chem, J., Zhao, J., Zhao, Y., Li, L., Zhang, H., “A modified procedure for the synthesis of 1- arylimidazoles”, Synthesis, 2661-2666, (2003).
  • Weinmann, H., Harre, M., Koeing, K., Merten, E., Tilestam, U., “Efficient and environmentally friendly Tetrahedron Lett., 43: 593-595, (2002). 2-amino-imidazole”,
  • Sarshar, S., Siev, D., Mjalli, A. M. M., “ Imidazole libraries on solid support”, Tetrahedron Lett. , 37, 835-838, (1996).
  • Wilson, K., Clark, J.H., “Solid acids and their uses as environmentally friendly catalysts in organic synthesis”, Pure Appl. Chem, 72: 1313-1319, (2000).
  • Kidwai, M., Mothsra, P., Bansal, V., Somvanshi, R. K., Ethayathulla, A. S., Dey, S., Singh, T., “One pot synthesis of highly substituted imidazoles using molecular iodine: A versatile catalyst”, J. Mol. Catal. A: Chem, 265: 177-182, (2007).
  • Heravi. M. M., Bakhtiari, K.H., Oskooie, H. A., Taheri, S.H., “Synthesis of 2,4,5-triaryl-imidazoles catalyzed by NiCl2.6H2O under heterogeneous system ”, J. Mol. Catal. A: Chem, 263: 279-281, (2007).
  • Siddiqui, S.A., Narkhede, U.C., Palimkar, S.S., Daniel, T., Lahoti, R.J., Srinivasan, K.V., “Room temperature ionic liquid promoted improved and rapid synthesis of 2,4,5-triarylimidazoles from aryl aldehydes and 1,2-diketones or α-hydroxyketones”, Tetrahedron, 61: 3539-3546, (2005).
  • Shaabani, A., Rahmati, A., “Silica sulfuric acid as an efficient and recoverable catalyst for the synthesis of trisubstituted imidazoles”, J.Mol.Catal.A:Chem., 249: 246-248, (2006).
  • Sivakumar, K., Kathivvel, A., Lalitha, A., “ Simple and efficient method for the synthesis of highly substituted imidazoles reagents”, Tetrahedron Letters, 51: 3018-3021,
  • zeolite-supported (2010).
  • Das, B., Sudhakar, C., Srinivas, Y., “Efficient synthesis of 5-substituted 2,3-Diphenyl and 5- substituted 1-Aryl-2,3-diphenyl imidazoles using polyethylene Glycol”, Synthetic Communications, 40: 2667-2675, (2010).
  • Shaabani, A., Maleki, A., Behnam, M., “Tandem oxidation process using Ceric ammonium nitrate : Three –Component synthesis of trisubstituted imidazoles under Aerobic oxidation conditions”, Synthetic Communications, 39: 102-110, (2009).

Yıl 2012, Cilt: 25 Sayı: 1, 29 - 34, 24.01.2012

Rahim Hekmatshoar , Rahim Hekmatshoar , Hajar Jahanbakhshı Farnoosh Mousavızadeh Reyhane Rahnamafar

Öz

Kaynakça

  • Zhu, J., Bienayme, Wiley-VCH,
  • Weinheim.Germany, Reactions”, (2005)
  • Orru, R.V.A., De Greef, M., “Recent advances in solution-phase multicomponent methodology for the synthesis of heterocyclic compounds”, Synthesis, 1471-1499, (2003).
  • Dembitsky, V.M., Gloriozova, T.A., Poroikov, V. V., “Novel antitumor agents: Marine sponge alkaloids, their synthetic analogs and derivatives”, Mini-rev. Med. Chem, 5: 319-336, (2005).
  • Nagawade, R.R., Shinde, D.B., “Zirconyl chloride- catalyzed multicomponent reaction of naphtoles: An expeditions synthesis of amido alkyl naphtols ”, Acta Chim Sslov, 54: 642-646, (2007).
  • Vallee, B.L., Auld, D.S., “Zinc coordination, function, and structure of zinc enzymes and other proteins”, Biochemistry, 29:5647-5659, (1990).
  • Liu, J., Zhao, Y., Zhou, Y., Li, L., Zhang, T.Y., Zhang, H.,“ Imidazolylidene carbene ligated palladium catalysis of the Heck reaction in the presence of air”, Org. Biomol. Chem., 1:3227-3231, (2003).
  • Grimmett, M.R., Katritzky, A.R. ,Ress, C. W., Scriven, E.F.V., “Comprehensive Heterocyclic Chemistry II” ,Pergamon Press , Oxford(eds), 3: 77-220, (1996).
  • Murry, J. A.,“ Synthetic methodology utilized to prepare substituted imidazole P38 MAP kinase inhibitors”, Curr. Opin. Drug Discovery Dev, 6: 945-965, (2003).
  • Narayana Murthy, S., Madhav, B., Nageswar, Y.V.D., “DABCO as a mild and efficient catalyst system for the synthesis of highly substituted imidazoles strategy”, Tetrahedron Letters, 51: 5252-5257, (2010). condensation
  • Schubert, H., Stodolka, H. J., “Diimidazole.II. Synthesis uberbruckten N,N´-Diimidazolen”, Prakt. Chem., 22: 130-139, (1963). und aromatisch
  • Tsuji, J., Sakai, K., Nemoto, H., Nagashima, H., “Iron and copper catalyzed reaction of benzylamine with carbon tetrachloride: Facile formation of 2,4,5- Triphenylimidazoline deravatives.” , J. Mol. Cata.l, 18: 169-176, (1983).
  • Frantz, E.D., Morency, L., Soheili, A., Murry, J. A., Grabowski, E. J. J., Tillyer, R.D., “Synthesis of substituted Imidazoles via organocatalysis”, Org. Lett., 6: 843-846, (2004).
  • Japp, F.R., Robinson, H.H., “ Constitution des lophins und des amarins”, Ber, 15: 1268-1270, (1882).
  • Wasserman, H.H., Long, Y. O., Zhang, R., Parr, J., “Alkenyl tricarbonyl derivatives of α-amino acids as trielectrophiles. substituted productes”, Tetrahedron Lett, 43: 3351- 3353, (2002). of heterocyclic
  • Liu, J., Chem, J., Zhao, J., Zhao, Y., Li, L., Zhang, H., “A modified procedure for the synthesis of 1- arylimidazoles”, Synthesis, 2661-2666, (2003).
  • Weinmann, H., Harre, M., Koeing, K., Merten, E., Tilestam, U., “Efficient and environmentally friendly Tetrahedron Lett., 43: 593-595, (2002). 2-amino-imidazole”,
  • Sarshar, S., Siev, D., Mjalli, A. M. M., “ Imidazole libraries on solid support”, Tetrahedron Lett. , 37, 835-838, (1996).
  • Wilson, K., Clark, J.H., “Solid acids and their uses as environmentally friendly catalysts in organic synthesis”, Pure Appl. Chem, 72: 1313-1319, (2000).
  • Kidwai, M., Mothsra, P., Bansal, V., Somvanshi, R. K., Ethayathulla, A. S., Dey, S., Singh, T., “One pot synthesis of highly substituted imidazoles using molecular iodine: A versatile catalyst”, J. Mol. Catal. A: Chem, 265: 177-182, (2007).
  • Heravi. M. M., Bakhtiari, K.H., Oskooie, H. A., Taheri, S.H., “Synthesis of 2,4,5-triaryl-imidazoles catalyzed by NiCl2.6H2O under heterogeneous system ”, J. Mol. Catal. A: Chem, 263: 279-281, (2007).
  • Siddiqui, S.A., Narkhede, U.C., Palimkar, S.S., Daniel, T., Lahoti, R.J., Srinivasan, K.V., “Room temperature ionic liquid promoted improved and rapid synthesis of 2,4,5-triarylimidazoles from aryl aldehydes and 1,2-diketones or α-hydroxyketones”, Tetrahedron, 61: 3539-3546, (2005).
  • Shaabani, A., Rahmati, A., “Silica sulfuric acid as an efficient and recoverable catalyst for the synthesis of trisubstituted imidazoles”, J.Mol.Catal.A:Chem., 249: 246-248, (2006).
  • Sivakumar, K., Kathivvel, A., Lalitha, A., “ Simple and efficient method for the synthesis of highly substituted imidazoles reagents”, Tetrahedron Letters, 51: 3018-3021,
  • zeolite-supported (2010).
  • Das, B., Sudhakar, C., Srinivas, Y., “Efficient synthesis of 5-substituted 2,3-Diphenyl and 5- substituted 1-Aryl-2,3-diphenyl imidazoles using polyethylene Glycol”, Synthetic Communications, 40: 2667-2675, (2010).
  • Shaabani, A., Maleki, A., Behnam, M., “Tandem oxidation process using Ceric ammonium nitrate : Three –Component synthesis of trisubstituted imidazoles under Aerobic oxidation conditions”, Synthetic Communications, 39: 102-110, (2009).
Toplam 27 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Bölüm Chemistry
Yazarlar

Rahim Hekmatshoar

Rahim Hekmatshoar

Hajar Jahanbakhshı

Farnoosh Mousavızadeh

Reyhane Rahnamafar

Yayımlanma Tarihi 24 Ocak 2012
Yayımlandığı Sayı Yıl 2012 Cilt: 25 Sayı: 1

Kaynak Göster

APA Hekmatshoar, R., Hekmatshoar, R., Jahanbakhshı, H., Mousavızadeh, F., vd. (2012). Synthesis of Trisubstituted Imidazoles Using Lewis and Bronsted Acid Catalysts. Gazi University Journal of Science, 25(1), 29-34.
AMA Hekmatshoar R, Hekmatshoar R, Jahanbakhshı H, Mousavızadeh F, Rahnamafar R. Synthesis of Trisubstituted Imidazoles Using Lewis and Bronsted Acid Catalysts. Gazi University Journal of Science. Ocak 2012;25(1):29-34.
Chicago Hekmatshoar, Rahim, Rahim Hekmatshoar, Hajar Jahanbakhshı, Farnoosh Mousavızadeh, ve Reyhane Rahnamafar. “Synthesis of Trisubstituted Imidazoles Using Lewis and Bronsted Acid Catalysts”. Gazi University Journal of Science 25, sy. 1 (Ocak 2012): 29-34.
EndNote Hekmatshoar R, Hekmatshoar R, Jahanbakhshı H, Mousavızadeh F, Rahnamafar R (01 Ocak 2012) Synthesis of Trisubstituted Imidazoles Using Lewis and Bronsted Acid Catalysts. Gazi University Journal of Science 25 1 29–34.
IEEE R. Hekmatshoar, R. Hekmatshoar, H. Jahanbakhshı, F. Mousavızadeh, ve R. Rahnamafar, “Synthesis of Trisubstituted Imidazoles Using Lewis and Bronsted Acid Catalysts”, Gazi University Journal of Science, c. 25, sy. 1, ss. 29–34, 2012.
ISNAD Hekmatshoar, Rahim vd. “Synthesis of Trisubstituted Imidazoles Using Lewis and Bronsted Acid Catalysts”. Gazi University Journal of Science 25/1 (Ocak 2012), 29-34.
JAMA Hekmatshoar R, Hekmatshoar R, Jahanbakhshı H, Mousavızadeh F, Rahnamafar R. Synthesis of Trisubstituted Imidazoles Using Lewis and Bronsted Acid Catalysts. Gazi University Journal of Science. 2012;25:29–34.
MLA Hekmatshoar, Rahim vd. “Synthesis of Trisubstituted Imidazoles Using Lewis and Bronsted Acid Catalysts”. Gazi University Journal of Science, c. 25, sy. 1, 2012, ss. 29-34.
Vancouver Hekmatshoar R, Hekmatshoar R, Jahanbakhshı H, Mousavızadeh F, Rahnamafar R. Synthesis of Trisubstituted Imidazoles Using Lewis and Bronsted Acid Catalysts. Gazi University Journal of Science. 2012;25(1):29-34.