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Volumn 20, Issue 2, 2013, Pages 627-632

An efficient synthesis of 2-substituted benzothiazoles in the presence of FeCl3/Montmorillonite K-10 under ultrasound irradiation

Author keywords

Aromatic aldehydes; Benzothiazoles; o Aminothiophenol; Ultrasound

Indexed keywords

ALDEHYDES; AROMATIC COMPOUNDS; CHEMICAL REACTIONS; IRON COMPOUNDS; ULTRASONICS;

EID: 84870243350     PISSN: 13504177     EISSN: 18732828     Source Type: Journal    
DOI: 10.1016/j.ultsonch.2012.09.010     Document Type: Article
Times cited : (65)

References (50)
  • 1
    • 0003989782 scopus 로고    scopus 로고
    • third ed. Addison-Wesley Longman, Ltd. England
    • T.L. Gilchrist Heterocyclic Chemistry third ed. 1998 Addison-Wesley Longman, Ltd. England
    • (1998) Heterocyclic Chemistry
    • Gilchrist, T.L.1
  • 4
    • 56449089532 scopus 로고    scopus 로고
    • Efficient aerobic oxidative synthesis of 2-substituted benzoxazoles, benzothiazoles, and benzimidazoles catalyzed by 4-methoxy-TEMPO
    • Y.X. Chen, L.F. Qian, W. Zhang, and B. Han Efficient aerobic oxidative synthesis of 2-substituted benzoxazoles, benzothiazoles, and benzimidazoles catalyzed by 4-methoxy-TEMPO Angew. Chem. Int. Ed. 47 2008 9330 9333
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 9330-9333
    • Chen, Y.X.1    Qian, L.F.2    Zhang, W.3    Han, B.4
  • 6
    • 77954498043 scopus 로고    scopus 로고
    • Efficient synthesis of 2-arylbenzothiazole derivatives with the aid of a low-valent titanium reagent
    • D.Q. Shi, S.F. Rong, and G.L. Dou Efficient synthesis of 2-arylbenzothiazole derivatives with the aid of a low-valent titanium reagent Synth. Commun. 40 2010 2302 2310
    • (2010) Synth. Commun. , vol.40 , pp. 2302-2310
    • Shi, D.Q.1    Rong, S.F.2    Dou, G.L.3
  • 7
    • 0028761154 scopus 로고
    • Studies on cure synergism. I. effect of safe zinc dithiocarbamates on NR vulcanization accelerated by thiazole-based accelerators
    • S.C. Debnath, and D.K. Basu Studies on cure synergism. I. effect of safe zinc dithiocarbamates on NR vulcanization accelerated by thiazole-based accelerators J. Appl. Polym. Sci. 52 1994 597 603
    • (1994) J. Appl. Polym. Sci. , vol.52 , pp. 597-603
    • Debnath, S.C.1    Basu, D.K.2
  • 8
    • 33746288153 scopus 로고    scopus 로고
    • Synthesis of 2-(4-substituted styryl)benzothiazoles by microwave irradiation
    • C.P. Ye, N.G. Wang, H.Q. Jia, and X.J. Xu Synthesis of 2-(4-substituted styryl)benzothiazoles by microwave irradiation Chin. J. Appl. Chem. 19 2002 1008 1010
    • (2002) Chin. J. Appl. Chem. , vol.19 , pp. 1008-1010
    • Ye, C.P.1    Wang, N.G.2    Jia, H.Q.3    Xu, X.J.4
  • 9
    • 0038356805 scopus 로고    scopus 로고
    • Sulfinyl- and sulfonyl-substituted 2-benzylbenzoxazoles and 2-benzylbenzothiazoles as potential photochromic compounds
    • A. Heynderickx, R. Guglielmetti, R. Dubest, J. Aubard, and A. Samat Sulfinyl-and sulfonyl-substituted 2-benzylbenzoxazoles and 2- benzylbenzothiazoles as potential photochromic compounds Synthesis 2003 1112 1116 (Pubitemid 36649120)
    • (2003) Synthesis , Issue.7 , pp. 1112-1116
    • Heynderickx, A.1    Guglielmetti, R.2    Dubest, R.3    Aubard, J.4    Samat, A.5
  • 10
    • 0037118366 scopus 로고    scopus 로고
    • Novel synthesis of 2-arylbenzothiazoles mediated by ceric ammonium nitrate (CAN)
    • R.H. Tale Novel synthesis of 2-arylbenzothiazoles mediated by ceric ammonium nitrate (CAN) Org. Lett. 4 2002 1641 1642
    • (2002) Org. Lett. , vol.4 , pp. 1641-1642
    • Tale, R.H.1
  • 11
    • 0035843438 scopus 로고    scopus 로고
    • Solid phase synthesis of benzothiazolyl compounds
    • DOI 10.1016/S0040-4039(01)00109-5, PII S0040403901001095
    • S. Mourtas, D. Gatos, and K. Barlos Solid phase synthesis of benzothiazolyl compounds Tetrahedron Lett. 42 2001 2201 2204 (Pubitemid 32187221)
    • (2001) Tetrahedron Letters , vol.42 , Issue.11 , pp. 2201-2204
    • Mourtas, S.1    Gatos, D.2    Barlos, K.3
  • 12
    • 1942456875 scopus 로고    scopus 로고
    • An efficient synthesis of benzothiazoles by direct condensation of carboxylic acids with 2-aminothiophenol under microwave irradiation
    • A.K. Chakraborti, C. Selvam, G. Kaur, and S. Bhagat An efficient synthesis of benzothiazoles by direct condensation of carboxylic acids with o-aminothiophenol under microwave irradiation Synlett 2004 851 855 (Pubitemid 38496909)
    • (2004) Synlett , Issue.5 , pp. 851-855
    • Chakraborti, A.K.1    Selvam, C.2    Kaur, G.3    Bhagat, S.4
  • 13
    • 0742322071 scopus 로고    scopus 로고
    • Liquid-phase synthesis of 2-substituted benzimidazoles, benzoxazoles and benzothiazoles
    • C.P. Chen, and Y.J. Chen Liquid-phase synthesis of 2-substituted benzimidazoles, benzoxazoles and benzothiazoles Tetrahedron Lett. 45 2004 113 115
    • (2004) Tetrahedron Lett. , vol.45 , pp. 113-115
    • Chen, C.P.1    Chen, Y.J.2
  • 14
    • 33847036694 scopus 로고    scopus 로고
    • Lawesson's reagent and microwaves: A new efficient access to benzoxazoles and benzothiazoles from carboxylic acids under solvent-free conditions
    • J.A. Seijas, M.P. Vazquez-Tato, M.R. Carballido-Reboredo, J. Crecente-Campo, and L. Romar-Lopez Lawesson's reagent and microwaves: a new efficient access to benzoxazoles and benzothiazoles from carboxylic acids under solvent-free conditions Synlett 2007 313 317
    • (2007) Synlett , pp. 313-317
    • Seijas, J.A.1    Vazquez-Tato, M.P.2    Carballido-Reboredo, M.R.3    Crecente-Campo, J.4    Romar-Lopez, L.5
  • 15
    • 0347758686 scopus 로고    scopus 로고
    • Tuning of wavelengths: Synthesis and photophysical studies of iridium complexes and their applications in organic light emitting devices
    • I.R. Laskar, and T.M. Chen Tuning of wavelengths: synthesis and photophysical studies of iridium complexes and their applications in organic light emitting devices Chem. Mater. 16 2004 111 117
    • (2004) Chem. Mater. , vol.16 , pp. 111-117
    • Laskar, I.R.1    Chen, T.M.2
  • 16
    • 1842638573 scopus 로고    scopus 로고
    • Room temperature ionic liquid promoted regioselective synthesis of 2-aryl benzimidazoles, benzoxazoles and benzthiazoles under ambient conditions
    • R.N. Nadaf, S.A. Siddiqui, T. Daniel, R.J. Lahoti, and K.V. Srinivasan Room temperature ionic liquid promoted regioselective synthesis of 2-aryl benzimidazoles, benzoxazoles and benzthiazoles under ambient conditions J. Mol. Catal. A: Chem. 214 2004 155 160
    • (2004) J. Mol. Catal. A: Chem. , vol.214 , pp. 155-160
    • Nadaf, R.N.1    Siddiqui, S.A.2    Daniel, T.3    Lahoti, R.J.4    Srinivasan, K.V.5
  • 17
    • 0347627369 scopus 로고    scopus 로고
    • Smart cleavage reactions: The synthesis of benzimidazoles and benzothiazoles from polymer-bound esters
    • DOI 10.1016/j.tetlet.2003.10.168
    • H. Matsushita, S.H. Lee, M. Joung, B. Clapham, and K.D. Janda Smart cleavage reactions: the synthesis of benzimidazoles and benzothiazoles from polymer-bound esters Tetrahedron Lett. 45 2004 313 316 (Pubitemid 37542268)
    • (2004) Tetrahedron Letters , vol.45 , Issue.2 , pp. 313-316
    • Matsushita, H.1    Lee, S.-H.2    Joung, M.3    Clapham, B.4    Janda, K.D.5
  • 18
    • 77950786935 scopus 로고    scopus 로고
    • Eco-friendly synthesis of 2-substituted benzothiazoles catalyzed by cetyltrimethyl ammonium bromide (CTAB) in water
    • X.L. Yang, C.M. Xu, S.M. Lin, J.X. Chen, J.C. Ding, H.Y. Wu, and W.K. Su Eco-friendly synthesis of 2-substituted benzothiazoles catalyzed by cetyltrimethyl ammonium bromide (CTAB) in water J. Braz. Chem. Soc. 21 2010 37 42
    • (2010) J. Braz. Chem. Soc. , vol.21 , pp. 37-42
    • Yang, X.L.1    Xu, C.M.2    Lin, S.M.3    Chen, J.X.4    Ding, J.C.5    Wu, H.Y.6    Su, W.K.7
  • 19
    • 55549133283 scopus 로고    scopus 로고
    • 2O)-catalyzed, eco-friendly, and efficient one-pot synthesis of 2-arylbenzothiazoles and 2-arylbenzoxazole in aqueous medium
    • 2O)-catalyzed, eco-friendly, and efficient one-pot synthesis of 2-arylbenzothiazoles and 2-arylbenzoxazole in aqueous medium Aust. J. Chem. 61 2008 905 909
    • (2008) Aust. J. Chem. , vol.61 , pp. 905-909
    • Pawar, S.S.1    Dekhane, D.V.2    Shingare, M.S.3    Thore, S.N.4
  • 20
    • 51549105076 scopus 로고    scopus 로고
    • Mild and highly efficient method for the synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles
    • K. Bahrami, M.M. Khodaei, and F. Naali Mild and highly efficient method for the synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles J. Org. Chem. 73 2008 6835 6837
    • (2008) J. Org. Chem. , vol.73 , pp. 6835-6837
    • Bahrami, K.1    Khodaei, M.M.2    Naali, F.3
  • 22
    • 43849095622 scopus 로고    scopus 로고
    • Electrooxidative cyclization of benzylideneaminothiophenols to the corresponding 2-arylbenzothiazoles
    • M. Okimoto, T. Yoshida, M. Hoshi, K. Hattori, M. Komata, K. Tomozawa, and T. Chiba Electrooxidative cyclization of benzylideneaminothiophenols to the corresponding 2-arylbenzothiazoles Heterocycles 75 2008 35 42
    • (2008) Heterocycles , vol.75 , pp. 35-42
    • Okimoto, M.1    Yoshida, T.2    Hoshi, M.3    Hattori, K.4    Komata, M.5    Tomozawa, K.6    Chiba, T.7
  • 23
    • 64949123222 scopus 로고    scopus 로고
    • Diversity oriented synthesis of benzimidazole and benzoxa/(thia)zole libraries through polymer-supported hypervalent iodine reagent
    • A. Kumar, R.A. Maurya, and P. Ahmad Diversity oriented synthesis of benzimidazole and benzoxa/(thia)zole libraries through polymer-supported hypervalent iodine reagent J. Comb. Chem. 11 2009 198 201
    • (2009) J. Comb. Chem. , vol.11 , pp. 198-201
    • Kumar, A.1    Maurya, R.A.2    Ahmad, P.3
  • 24
    • 0347720714 scopus 로고    scopus 로고
    • Synthesis of 2-arylbenzothiazoles from 2-aminobenzenethiol and aryl aldehydes catalyzed by scandium triflate
    • T. Itoh, K. Nagata, H. Ishikawa, and A. Ohsawa Synthesis of 2-arylbenzothiazoles from 2-aminobenzenethiol and aryl aldehydes catalyzed by scandium triflate Heterocycles 62 2004 197 201
    • (2004) Heterocycles , vol.62 , pp. 197-201
    • Itoh, T.1    Nagata, K.2    Ishikawa, H.3    Ohsawa, A.4
  • 25
    • 67650495697 scopus 로고    scopus 로고
    • Trichloroisocyanuric acid (TCCA) as a mild and efficient catalyst for the synthesis of 2-arylbenzothiazoles
    • H.L. Xiao, J.X. Chen, M.C. Liu, D.J. Zhu, J.C. Ding, and H.Y. Wu Trichloroisocyanuric acid (TCCA) as a mild and efficient catalyst for the synthesis of 2-arylbenzothiazoles Chem. Lett. 38 2009 170 171
    • (2009) Chem. Lett. , vol.38 , pp. 170-171
    • Xiao, H.L.1    Chen, J.X.2    Liu, M.C.3    Zhu, D.J.4    Ding, J.C.5    Wu, H.Y.6
  • 26
    • 33745183168 scopus 로고    scopus 로고
    • A simple iodine-promoted synthesis of 2-substituted benzothiazoles by condensation of aldehydes with 2-aminothiophenol
    • DOI 10.1246/cl.2006.460
    • Y. Li, Y.L. Wang, and J.Y. Wang A simple iodine-promoted synthesis of 2-substituted benzothiazoles by condensation of aldehydes with 2-aminothiophenol Chem. Lett. 35 2006 460 461 (Pubitemid 44031251)
    • (2006) Chemistry Letters , vol.35 , Issue.4 , pp. 460-461
    • Li, Y.1    Wang, Y.-L.2    Wang, J.-Y.3
  • 27
    • 74949129774 scopus 로고    scopus 로고
    • Perchloric acid-doped polyaniline as an efficient and reusable catalyst for the synthesis of 2-substituted benzothiazoles
    • M. Abdollahi-Alibeik, and S. Poorirani Perchloric acid-doped polyaniline as an efficient and reusable catalyst for the synthesis of 2-substituted benzothiazoles Phosphorus Sulfur Silicon Relat. Elem. 184 2009 3182 3190
    • (2009) Phosphorus Sulfur Silicon Relat. Elem. , vol.184 , pp. 3182-3190
    • Abdollahi-Alibeik, M.1    Poorirani, S.2
  • 28
    • 4544382219 scopus 로고    scopus 로고
    • Solvent-free synthesis of 2-aryl and 2-alkylbenzothiazoles on silica gel under microwave irradiation
    • DOI 10.1081/SCC-200026663
    • M. Kodomari, Y. Tamaru, and T. Aoyama Solvent-free synthesis of 2-aryl and 2-alkyl benzothiazoles on silica gel under microwave irradiation Synth. Commun. 34 2004 3029 3036 (Pubitemid 39223768)
    • (2004) Synthetic Communications , vol.34 , Issue.16 , pp. 3029-3036
    • Kodomari, M.1    Tamaru, Y.2    Aoyama, T.3
  • 29
    • 72249123528 scopus 로고    scopus 로고
    • PTSA catalyzed simple and green synthesis of benzothiazole derivatives in water
    • N. Azizi, A.K. Amiri, R. Baghi, M. Bolourtchian, and M.M. Hashemi PTSA catalyzed simple and green synthesis of benzothiazole derivatives in water Monatsh. Chem. 140 2009 1471 1473
    • (2009) Monatsh. Chem. , vol.140 , pp. 1471-1473
    • Azizi, N.1    Amiri, A.K.2    Baghi, R.3    Bolourtchian, M.4    Hashemi, M.M.5
  • 30
    • 65249123460 scopus 로고    scopus 로고
    • Mechanistic study of oxidative aromatization using activated carbonmolecular oxygen system in the synthesis of 2-arylbenzazoles: Focus on the role of activated carbon
    • Y. Kawashita, J. Yanagi, T. Fujii, and M. Hayashi Mechanistic study of oxidative aromatization using activated carbonmolecular oxygen system in the synthesis of 2-arylbenzazoles: focus on the role of activated carbon Bull. Chem. Soc. Jpn. 82 2009 482 488
    • (2009) Bull. Chem. Soc. Jpn. , vol.82 , pp. 482-488
    • Kawashita, Y.1    Yanagi, J.2    Fujii, T.3    Hayashi, M.4
  • 31
    • 2442642622 scopus 로고    scopus 로고
    • An efficient and green synthesis of 2-arylbenzothiazoles in an ionic liquid, [pmIm]Br under microwave irradiation
    • DOI 10.1246/cl.2004.274
    • B.C. Ranu, R. Jana, and S.S. Dey An efficient and green synthesis of 2-arylbenzothiazoles in an ionic liquid, [pmim]Br under microwave irradiation Chem. Lett. 33 2004 274 275 (Pubitemid 38661958)
    • (2004) Chemistry Letters , vol.33 , Issue.3 , pp. 274-275
    • Ranu, B.C.1    Jana, R.2    Dey, S.S.3
  • 32
    • 59049106830 scopus 로고    scopus 로고
    • Bakers' yeast catalyzed synthesis of benzothiazoles in an organic medium
    • U.R. Pratap, J.R. Mali, D.V. Jawale, and R.A. Mane Bakers' yeast catalyzed synthesis of benzothiazoles in an organic medium Tetrahedron Lett. 50 2009 1352 1354
    • (2009) Tetrahedron Lett. , vol.50 , pp. 1352-1354
    • Pratap, U.R.1    Mali, J.R.2    Jawale, D.V.3    Mane, R.A.4
  • 33
    • 77954591753 scopus 로고    scopus 로고
    • Synthesis of 1,2-disubstituted benzimidazoles, 2-substituted benzimidazoles and 2-substituted benzothiazoles in SDS micelles
    • K. Bahrami, M.M. Khodaei, and A. Nejatia Synthesis of 1,2-disubstituted benzimidazoles, 2-substituted benzimidazoles and 2-substituted benzothiazoles in SDS micelles Green Chem. 12 2010 1237 1241
    • (2010) Green Chem. , vol.12 , pp. 1237-1241
    • Bahrami, K.1    Khodaei, M.M.2    Nejatia, A.3
  • 34
    • 78049402197 scopus 로고    scopus 로고
    • Bienzymatic synthesis of benzothia/(oxa)zoles in aqueous medium
    • A. Kumar, S. Sharma, and R.A. Maurya Bienzymatic synthesis of benzothia/(oxa)zoles in aqueous medium Tetrahedron Lett. 51 2010 6224 6226
    • (2010) Tetrahedron Lett. , vol.51 , pp. 6224-6226
    • Kumar, A.1    Sharma, S.2    Maurya, R.A.3
  • 35
    • 79151481767 scopus 로고    scopus 로고
    • 5 mediated rapid condensation of 2-aminothiophenol with aromatic aldehydes at ambient temperature
    • 5 mediated rapid condensation of 2-aminothiophenol with aromatic aldehydes at ambient temperature Chin. Chem. Lett. 21 2010 790 793
    • (2010) Chin. Chem. Lett. , vol.21 , pp. 790-793
    • Nalage, S.V.1    Bhosale, S.V.2    Bhosale, D.S.3    Jadhav, W.N.4
  • 36
    • 61849146918 scopus 로고    scopus 로고
    • Water-promoted Dowex 50W catalyzed highly efficient green protocol for 2-arylbenzothiazole formation
    • C. Mukhopadhyay, and A. Datta Water-promoted Dowex 50W catalyzed highly efficient green protocol for 2-arylbenzothiazole formation J. Heterocycl. Chem. 46 2009 91 95
    • (2009) J. Heterocycl. Chem. , vol.46 , pp. 91-95
    • Mukhopadhyay, C.1    Datta, A.2
  • 39
    • 33847294239 scopus 로고    scopus 로고
    • Sonochemistry and the environment - Providing a "green" link between chemistry, physics and engineering
    • DOI 10.1016/j.ultsonch.2006.10.008, PII S1350417706001568
    • T.J. Mason Sonochemistry and the environment-Providing a "green" link between chemistry, physics and engineering Ultrason. Sonochem. 14 2007 476 483 (Pubitemid 46330095)
    • (2007) Ultrasonics Sonochemistry , vol.14 , Issue.4 , pp. 476-483
    • Mason, T.J.1
  • 40
    • 33646107336 scopus 로고    scopus 로고
    • Some applications of ultrasound irradiation in organic synthesis
    • J.T. Li, S.X. Wang, G.F. Chen, and T.S. Li Some applications of ultrasound irradiation in organic synthesis Curr. Org. Synth. 2 2005 415 436
    • (2005) Curr. Org. Synth. , vol.2 , pp. 415-436
    • Li, J.T.1    Wang, S.X.2    Chen, G.F.3    Li, T.S.4
  • 42
    • 33845281365 scopus 로고
    • Michael additions of nitroalkanes to α,β-unsaturated carbonyl compounds using potassium fluoride/basic alumina
    • D.E. Bergbreiter, and J.J. Lalonde Michael additions of nitroalkanes to α,β-unsaturated carbonyl compounds using potassium fluoride/basic alumina J. Org. Chem. 52 1987 1601 1603
    • (1987) J. Org. Chem. , vol.52 , pp. 1601-1603
    • Bergbreiter, D.E.1    Lalonde, J.J.2
  • 44
    • 84870240860 scopus 로고    scopus 로고
    • Preparation of benzil from benzoin by ferric chloride supported on montmorillonite K10 as oxidant
    • F.Q. Li Preparation of benzil from benzoin by ferric chloride supported on montmorillonite K10 as oxidant Appl. Chem. Ind. 40 2011 459 461
    • (2011) Appl. Chem. Ind. , vol.40 , pp. 459-461
    • Li, F.Q.1
  • 45
    • 0037350525 scopus 로고    scopus 로고
    • The michael reaction catalyzed by KF/basic alumina under ultrasound irradiation
    • J.T. Li, G.F. Chen, W.Z. Xu, and T.S. Li The michael reaction catalyzed by KF/basic alumina under ultrasound irradiation Ultrason. Sonochem. 10 2003 115 118
    • (2003) Ultrason. Sonochem. , vol.10 , pp. 115-118
    • Li, J.T.1    Chen, G.F.2    Xu, W.Z.3    Li, T.S.4
  • 46
    • 0037405276 scopus 로고    scopus 로고
    • Ultrasound promoted synthesis of 2-aroyl-1,3,5-triaryl-4-carbethoxy-4- cyanocyclohexanols
    • J.T. Li, G.F. Chen, W.Z. Yang, and T.S. Li Ultrasound promoted synthesis of 2-aroyl-1,3,5-triaryl-4-carbethoxy-4-cyanocyclohexanols Ultrason. Sonochem. 10 2003 123 126
    • (2003) Ultrason. Sonochem. , vol.10 , pp. 123-126
    • Li, J.T.1    Chen, G.F.2    Yang, W.Z.3    Li, T.S.4
  • 48
    • 80052053737 scopus 로고    scopus 로고
    • Efficient method for deprotection of oximes to corresponding carbonyl compounds catalyzed by silica sulfuric acid
    • J.T. Li, X.T. Meng, L. Liu, and G.F. Chen Efficient method for deprotection of oximes to corresponding carbonyl compounds catalyzed by silica sulfuric acid Chin. J. Org. Chem. 31 2011 733 736
    • (2011) Chin. J. Org. Chem. , vol.31 , pp. 733-736
    • Li, J.T.1    Meng, X.T.2    Liu, L.3    Chen, G.F.4


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