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Volumn 42, Issue 8, 2012, Pages 1184-1191

Efficient and novel method for thiocyanation of aromatic compounds using trichloroisocyanuric acid/ammonium thiocyanate/wet SiO 2

Author keywords

Aromatic; Thiocyanation; Trichloroisocyanuric acid; Wet SiO 2

Indexed keywords

AROMATIC COMPOUND; CYANURIC ACID; HETEROCYCLIC COMPOUND; SILICON DIOXIDE; SYMCLOSENE; THIOCYANATE AMMONIUM; THIOCYANIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84857614012     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.537424     Document Type: Article
Times cited : (35)

References (36)
  • 1
    • 0000817070 scopus 로고
    • Wiley: New York
    • (a) Wood, J. L. Organic Reactions; Wiley: New York, 1967; vol. 3, pp. 240-266;
    • (1967) Organic Reactions , vol.3 , pp. 240-266
    • Wood, J.L.1
  • 2
    • 0027433854 scopus 로고
    • Structure correction and synthesis of the naturally occurring benzothiazinone BMY 40662
    • DOI 10.1021/jo00073a057
    • (b) Kelly, T. R.; Kim, M. H.; Curtis, A. D. M. Structure correction and synthesis of the naturally occurring benzothiazinone BMY 40662. J. Org. Chem. 1993, 58, 5855-5857. (Pubitemid 23351756)
    • (1993) Journal of Organic Chemistry , vol.58 , Issue.21 , pp. 5855-5857
    • Kelly, T.R.1    Kim, M.H.2    Curtis, A.D.M.3
  • 3
    • 0028928412 scopus 로고
    • Thiocyanate as a versatile synthetic unit: Efficient conversion of ArSCN to aryl alkyl sulfides and aryl thioesters
    • (a) Toste, F. D.; Laronde, F.; Still, W. J. Thiocyanate as a versatile synthetic unit: Efficient conversion of ArSCN to aryl alkyl sulfides and aryl thioesters. Tetrahedron Lett. 1995, 36, 2949-2952;
    • (1995) Tetrahedron Lett. , vol.36 , pp. 2949-2952
    • Toste, F.D.1    Laronde, F.2    Still, W.J.3
  • 4
    • 0141588652 scopus 로고
    • Thiocyanation of indole: Some reactions of 3-thiocyanoindole
    • (b) Grant, M. S.; Snyder, H. R. Thiocyanation of indole: Some reactions of 3-thiocyanoindole. J. Am. Chem. Soc. 1960, 82, 2742-2744
    • (1960) J. Am. Chem. Soc. , vol.82 , pp. 2742-2744
    • Grant, M.S.1    Snyder, H.R.2
  • 6
    • 84857547665 scopus 로고
    • Photochemical thiocyanation of aromatic compounds
    • (a) Taylor, E. C.; Kienzle, F. Photochemical thiocyanation of aromatic compounds. Synthesis 1972, 38-38;
    • (1972) Synthesis , pp. 38-38
    • Taylor, E.C.1    Kienzle, F.2
  • 7
    • 0141588647 scopus 로고
    • Aromatic thiocyanation by a mixture of antimony(V) chloride and lead(II) thiocyanate
    • (b) Uemura, S.; Onoe, A.; Okazaki, H.; Okano, M. Aromatic thiocyanation by a mixture of antimony(V) chloride and lead(II) thiocyanate. Bull. Chem. Soc. Jpn. 1975, 48, 619-620
    • (1975) Bull. Chem. Soc. Jpn. , vol.48 , pp. 619-620
    • Uemura, S.1    Onoe, A.2    Okazaki, H.3    Okano, M.4
  • 8
    • 0001548384 scopus 로고
    • Novel and direct nucleophilic sulfenylation and thiocyanation of phenol ethers using a hypervalent iodine(III) reagent
    • (c) Kita, Y.; Takada, T.; Mihara, S.; Whelan, B. A.; Tohma, H. Novel and direct nucleophilic sulfenylation and thiocyanation of phenol ethers using a hypervalent iodine(III) reagent. J. Org. Chem. 1995, 60, 7144-7148;
    • (1995) J. Org. Chem. , vol.60 , pp. 7144-7148
    • Kita, Y.1    Takada, T.2    Mihara, S.3    Whelan, B.A.4    Tohma, H.5
  • 9
    • 0012833621 scopus 로고    scopus 로고
    • Preparation of arylthiocyanates using N,N'-dibromo-N,N'-bis(2, 5-dimethylbenzenesulphonyl) ethylenediamine and N,N-dibromo-2,5- dimethylbenzenesulphonamide in the presence of KSCN as a novel thiocyanating reagent
    • (d) Khazei, A.; Alizadeh, A.; Vaghei, R. G. Preparation of arylthiocyanates using N,N′-Dibromo-N, N′-bis(2,5- dimethylbenzenesulphonyl) ethylenediamine and N,N-dibromo-2,5-dimethylbenzene sulphonamide in the presence of KSCN as a novel thiocyanating reagent. Molecules 2001, 6, 253-257. (Pubitemid 38982468)
    • (2001) Molecules , vol.6 , Issue.3 , pp. 253-257
    • Khazaei, A.1    Alizadeh, A.2    Vaghei, R.G.3
  • 10
    • 0033524666 scopus 로고    scopus 로고
    • A direct synthesis of aryl thiocyanates using cerium(IV) ammonium nitrate
    • DOI 10.1016/S0040-4039(98)02563-5, PII S0040403998025635
    • (a) Nair, V.; George, T. G.; Nair, L. G.; Panicker, S. B. A Direct synthesis of aryl thicyanates using cerium(IV) ammonium nitrate. Tetrahedron Lett. 1999, 40, 1195-1196; (Pubitemid 29039820)
    • (1999) Tetrahedron Letters , vol.40 , Issue.6 , pp. 1195-1196
    • Nair, V.1    George, T.G.2    Nair, L.G.3    Panicker, S.B.4
  • 11
    • 1642276015 scopus 로고    scopus 로고
    • Iodine/MeOH: A novel and efficient reagent system for thiocyanation of aromatics and heteroaromatics
    • DOI 10.1016/j.tetlet.2004.02.073, PII S0040403904003880
    • (b) Yadav, J. S.; Reddy, S. B. V.; Shubashree, S.; Sadashiv, K. Iodine/MeOH: A novel and efficient reagent system for thiocyanation of aromatics and heteroaromatics. Tetrahedron Lett. 2004, 45, 2951-2954; (Pubitemid 38367823)
    • (2004) Tetrahedron Letters , vol.45 , Issue.14 , pp. 2951-2954
    • Yadav, J.S.1    Reddy, B.V.S.2    Shubashree, S.3    Sadashiv, K.4
  • 12
    • 17744364542 scopus 로고    scopus 로고
    • Ferric(III) chloride-promoted electrophilic thiocyanation of aromatic and heteroaromatic compounds
    • DOI 10.1055/s-2005-861852, Z16504SS
    • (c) Yadav, J. S.; Reddy, B. V. S.; Krishna,A. D.; Reddy, C. S.; Narsaiah, A. V. Ferric(III) chloride-promoted electrophilic thiocyanation of aromatic and heteroaromatic compounds. Synthesis 2005, 961-964 (Pubitemid 40577264)
    • (2005) Synthesis , Issue.6 , pp. 961-964
    • Yadav, J.S.1    Reddy, B.V.S.2    Krishna, A.D.3    Suresh Reddy, Ch.4    Narsaiah, A.V.5
  • 13
    • 23044459885 scopus 로고    scopus 로고
    • Regioselective thiocyanation of aromatic and heteroaromatic compounds using ammonium thiocyanate and oxone
    • DOI 10.1016/j.tetlet.2005.06.132, PII S0040403905014164
    • (d) Wu, G.; Liu, Q.; Shen, Y.; Wu, W.; Wu, L. Regioselective thiocyanation of aromatic and heteroaromatic compounds using ammonium thiocyanate and oxone. Tetrahedron Lett. 2005, 46, 5831-5834. (Pubitemid 41073424)
    • (2005) Tetrahedron Letters , vol.46 , Issue.35 , pp. 5831-5834
    • Wu, G.1    Liu, Q.2    Shen, Y.3    Wu, W.4    Wu, L.5
  • 14
    • 38149031681 scopus 로고    scopus 로고
    • DDQ-promoted thiocyanation of aromatic and heteroaromatic compounds
    • (a) Memarian, H. R.; Mohammadpoor-Baltork, I.; Nikoofar, K. DDQ-promoted thiocyanation of aromatic and heteroaromatic compounds. Can. J. Chem. 2007, 85, 930-937;
    • (2007) Can. J. Chem. , vol.85 , pp. 930-937
    • Memarian, H.R.1    Mohammadpoor-Baltork, I.2    Nikoofar, K.3
  • 15
    • 37349055154 scopus 로고    scopus 로고
    • Efficient and novel method for thiocyanation of aromatic and heteroaromatic compounds using bromodimethylsulfonium bromide and ammonium thiocyanate
    • DOI 10.1055/s-2007-992367
    • (b) Bhalerao, D. S.; Agamanchi, K. G. Efficient and novel method for thiocyanation of aromatic and hetero-aromatic compounds using bromodimethylsulfonium bromide and ammonium thiocyanate. Synlett 2007, 2952-2956; (Pubitemid 350284435)
    • (2007) Synlett , Issue.19 , pp. 2952-2956
    • Bhalerao, D.S.1    Akamanchi, K.G.2
  • 16
    • 67650299485 scopus 로고    scopus 로고
    • Facile method for thiocyanation of activated arenes using iodic acid in combination with ammonium thiocyanate
    • (c) Mahajan, U.; Akamanchi, K. Facile method for thiocyanation of activated arenes using iodic acid in combination with ammonium thiocyanate. Synth. Commun. 2009, 39, 2674-2682
    • (2009) Synth. Commun. , vol.39 , pp. 2674-2682
    • Mahajan, U.1    Akamanchi, K.2
  • 17
    • 47249139524 scopus 로고    scopus 로고
    • Thiocyanation of aromatic and heteroaromatic compounds using ammonium thiocyanate and I2O5
    • DOI 10.1080/00397910802139254, PII 794881130
    • 5. Synth. Commun. 2008, 38, 2367-2373; (Pubitemid 351990098)
    • (2008) Synthetic Communications , vol.38 , Issue.14 , pp. 2367-2373
    • Wu, J.1    Wu, G.2    Wu, L.3
  • 18
    • 73949155910 scopus 로고    scopus 로고
    • Efficient thiocyanation of indoles using para-toluene sulfonic acid
    • (e) Das, B.; Kumar, A. S. Efficient thiocyanation of indoles using para-toluene sulfonic acid. Synth. Commun. 2010, 40, 337-341.
    • (2010) Synth. Commun. , vol.40 , pp. 337-341
    • Das, B.1    Kumar, A.S.2
  • 19
    • 0037195711 scopus 로고    scopus 로고
    • Tetramethylammonium dichloroiodate: An efficient and environmentally friendly iodination reagent for iodination of aromatic compounds under mild and solvent-free conditions
    • DOI 10.1021/jo0264628
    • (a) Hajipour,A. R.; Arbabian, M.; Ruoho, A. E. Tetramethylammonium dichloroiodate: An efficient and environmentally friendly iodination reagent for iodination of aromatic compounds under mild and solvent-free conditions. J. Org. Chem. 2002, 67, 8622-8624; (Pubitemid 35403015)
    • (2002) Journal of Organic Chemistry , vol.67 , Issue.24 , pp. 8622-8624
    • Hajipour, A.R.1    Arbabian, M.2    Ruoho, A.E.3
  • 20
    • 0030031144 scopus 로고    scopus 로고
    • Sulfuric acid on silica-gel: An inexpensive catalyst for aromatic nitration
    • DOI 10.1016/0040-4039(95)02174-4
    • (b) Sedin, Z.; Zaldivar, J. M.; Marziano, N. C.; Tortato, C. Sulfuric acid on silica-gel: An inexpensive catalyst for aromatic nitration. Tetrahedron Lett. 1996, 37, 513-516. (Pubitemid 26040331)
    • (1996) Tetrahedron Letters , vol.37 , Issue.4 , pp. 513-516
    • Riego, J.M.1    Sedin, Z.2    Zaldivar, J.M.3    Marziano, N.C.4    Tortato, C.5
  • 21
    • 0000604235 scopus 로고
    • Photochemistry of ketones adsorbed on porous silica
    • Turro, N. J. Photochemistry of ketones adsorbed on porous silica. Tetrahedron 1987, 43, 1589-1616.
    • (1987) Tetrahedron , vol.43 , pp. 1589-1616
    • Turro, N.J.1
  • 22
    • 23944476931 scopus 로고    scopus 로고
    • Trichloroisocyanuric acid (TCCA)
    • DOI 10.1055/s-2005-872237, V13305ST
    • (a) Barros, J. C. Trichloroisocyanuric acid (TCCA). Synlett 2005, 2115-2116; (Pubitemid 41207627)
    • (2005) Synlett , Issue.13 , pp. 2115-2116
    • Barros, J.C.1
  • 23
    • 0036326850 scopus 로고    scopus 로고
    • Trichloroisocyanuric acid: A safe and efficient oxidant
    • (b) Tilstam, U.; Weinmann, H. Trichloroisocyanuric acid: A safe and efficient oxidant. Org. Process Res. Dev. 2002, 6, 384-393;
    • (2002) Org. Process Res. Dev. , vol.6 , pp. 384-393
    • Tilstam, U.1    Weinmann, H.2
  • 24
    • 0036459104 scopus 로고    scopus 로고
    • Trichloroisocyanuric acid: An alternate green route for the transformation of alkenes into epoxides
    • (c) Wengert, M.; Sanseverino, A. M.; de Mattos, M. C. S. Trichloroisocyanuric acid: An alternate green route for the transformation of alkenes into epoxides. J. Braz. Chem. Soc. 2002, 13, 700-703;
    • (2002) J. Braz. Chem. Soc. , vol.13 , pp. 700-703
    • Wengert, M.1    Sanseverino, A.M.2    De Mattos, M.C.S.3
  • 25
    • 3843057831 scopus 로고    scopus 로고
    • Preparation of alkyl nitrates, nitrites, and thiocyanates from alcohols utilizing trichloroisocyanuric acid with triphenylphosphine
    • DOI 10.1081/SCC-200025580
    • (d) Hiegel, G. A.; Nguyen, J.; Zhou, Y. Preparation of alkyl nitrates, nitrites, and thiocyanates from alcohols utilizing trichloroisocyanuric acid with triphenylphosphine. Synth. Commun. 2004, 34, 2507-2511. (Pubitemid 39038426)
    • (2004) Synthetic Communications , vol.34 , Issue.14 , pp. 2507-2511
    • Hiegel, G.A.1    Nguyen, J.2    Zhou, Y.3
  • 26
    • 0034805842 scopus 로고    scopus 로고
    • Trichloroisocyanuric acid as a mild and efficient catalyst for thioacetalization and transthio-acetalization reactions
    • (a) Firouzabadi, H.; Iranpoor, N.; Hazarkhani, H. Trichloroisocyanuric Acid as a mild and efficient catalyst for thioacetalization and transthio-acetalization reactions. Synlett 2001, 1641-1643; (Pubitemid 32929784)
    • (2001) Synlett , Issue.10 , pp. 1641-1643
    • Firouzabadi, H.1    Iranpoor, N.2    Hazarkhani, H.3
  • 27
    • 0035098518 scopus 로고    scopus 로고
    • A selective and convenient oxidation of sulfides to sulfoxides with trichloroisocyanuric acid
    • DOI 10.1081/SCC-100000205
    • (b) Xiog, Z. X.; Huang, N. P.; Zhong, P. A selective and convenient oxidation of sulfides to sulfoxides with trichloroisocyanuric acid. Synth.Commun. 2001, 31, 245-248. (Pubitemid 32201746)
    • (2001) Synthetic Communications , vol.31 , Issue.2 , pp. 245-248
    • Xiong, Z.-X.1    Huang, N.-P.2    Zhong, P.3
  • 28
    • 0037287084 scopus 로고    scopus 로고
    • 2 as a novel heterogeneous system for the selective mononitration of phenols under mild conditions
    • 2 as a novel heterogeneous system for the selective mononitration of phenols under mild conditions. Synlett 2003, 191-194; (Pubitemid 36249934)
    • (2003) Synlett , Issue.2 , pp. 191-194
    • Zolfigol, M.A.1    Ghaemi, E.2    Madrakian, E.3
  • 29
    • 0242575792 scopus 로고    scopus 로고
    • 2 as an Efficient System for the Selective Dinitration of Phenols under Solvent-free Conditions
    • (b) Zolfigol, M. A.; Madrakian, E.; Ghaemi, E. A Selective and convenient oxidation of sulfides to sulfoxides with trichloroisocyanuric acid. Trichloroisocyanuric acid/NaNO2/wet SiO2 as an efficient system for the selective dinitration of phenols under solvent-free conditions. Synlett 2003, 2222-2224. (Pubitemid 37430796)
    • (2003) Synlett , Issue.14 , pp. 2222-2224
    • Zolfigol, M.A.1    Madrakian, E.2    Ghaemi, E.3
  • 30
    • 61849167441 scopus 로고    scopus 로고
    • 2 system
    • (a) Akhlaghinia, B.; Rahmani, M. Mild and efficient iodination of aromatic compounds with trichloroisocyanuric acid/I2/wet SiO2 system. Turk. J. Chem. 2009, 33, 67-72;
    • (2009) Turk. J. Chem. , vol.33 , pp. 67-72
    • Akhlaghinia, B.1    Rahmani, M.2
  • 33
    • 37049049572 scopus 로고
    • The infrared spectrum of thiocyanogen and thiocyanogen halides
    • Nelson, M. J.; Pullin, A. D. E. The infrared spectrum of thiocyanogen and thiocyanogen halides. J. Chem. Soc. 1960, 604-612.
    • (1960) J. Chem. Soc. , pp. 604-612
    • Nelson, M.J.1    Pullin, A.D.E.2
  • 35
    • 0346607454 scopus 로고
    • 2,2-Diphenyl-3,3-dimethylethylenimine and related compounds
    • Kissman, H. M.; Tarbell, D. S.; Williams, J. 2,2-Diphenyl-3,3- dimethylethylenimine and Related Compounds. J. Am. Chem. Soc. 1953, 75, 2959-2962.
    • (1953) J. Am. Chem. Soc. , vol.75 , pp. 2959-2962
    • Kissman, H.M.1    Tarbell, D.S.2    Williams, J.3
  • 36
    • 18744409788 scopus 로고    scopus 로고
    • Efficient and mild oxidative nuclear thiocyanation of activated aromatic compounds using ammonium thiocyanate and diacetoxyiodobenzene
    • DOI 10.1081/SCC-200054770
    • Karade, N. N.; Tiwari, G. B.; Shirodkar, S. G.; Dhoot, B. M. Efficient and mild oxidative nuclear thiocyanation of activated aromatic compounds using ammonium thiocyanate and diacetoxyiodobenzene. Synth. Commun. 2005, 35, 1197-1201. (Pubitemid 40677467)
    • (2005) Synthetic Communications , vol.35 , Issue.9 , pp. 1197-1201
    • Karade, N.N.1    Tiwari, G.B.2    Shirodkar, S.G.3    Dhoot, B.M.4


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