메뉴 건너뛰기




Volumn 41, Issue 9, 2011, Pages 1257-1266

One-pot synthesis of salicylanilides by direct amide bond formation from salicyclic acid under microwave irradiation

Author keywords

Microwave irradiation; salicylanilide; synthesis

Indexed keywords

AMIDE; AROMATIC AMIDE; AROMATIC AMINE; PHOSPHORUS DERIVATIVE; PHOSPHORUS TRICHLORIDE; SALICYLANILIDE DERIVATIVE; SALICYLIC ACID; UNCLASSIFIED DRUG;

EID: 79953663393     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.481745     Document Type: Article
Times cited : (6)

References (39)
  • 1
    • 0029796373 scopus 로고    scopus 로고
    • New directions in antibacterial research
    • DOI 10.1021/jm960294s
    • (a) Chu, D. T. W.; Plattner, J. J.; Katz, L. New directions in antibacterial research. J. Med. Chem. 1996, 39, 3853-3874; (Pubitemid 26327422)
    • (1996) Journal of Medicinal Chemistry , vol.39 , Issue.20 , pp. 3853-3874
    • Chu, D.T.W.1    Plattner, J.J.2    Katz, L.3
  • 2
    • 2942567819 scopus 로고    scopus 로고
    • Developments in peptide and amide synthesis
    • DOI 10.1016/j.cbpa.2004.03.002, PII S1367593104000444
    • (b) Albericio, F. Developments in peptide and amide synthesis. Curr. Opin. Chem. Biol. 2004, 8, 211-221; (Pubitemid 38759395)
    • (2004) Current Opinion in Chemical Biology , vol.8 , Issue.3 , pp. 211-221
    • Albericio, F.1
  • 3
    • 1342279609 scopus 로고    scopus 로고
    • Salicylanilides as inhibitors of the protein tyrosine kinase epidermal growth factor receptor
    • DOI 10.1016/j.ejmech.2003.09.010
    • (c) Liechti, C.; Sé quin, U.; Bold, G.; Furet, P.; Meyer, T.; Traxler, P. Salicylanilides as inhibitors of the protein tyrosine kinase epidermal growth factor receptor. J. Med. Chem. 2004, 39, 11-26; (Pubitemid 38251209)
    • (2004) European Journal of Medicinal Chemistry , vol.39 , Issue.1 , pp. 11-26
    • Liechti, C.1    Sequin, U.2    Bold, G.3    Furet, P.4    Meyer, T.5    Traxler, P.6
  • 5
    • 27944471274 scopus 로고    scopus 로고
    • Acryloylamino-salicylanilides as EGFR PTK inhibitors
    • DOI 10.1016/j.bmcl.2005.06.088, PII S0960894X05008577
    • (e) Deng, W.; Guo, Z. R.; Guo, Y. S.; Feng, Z. Q.; Jiang, Y.; Chu, F. M. Acryloylamino-salicylanilides as EGFR PTK inhibitors. Bioorg. Med. Chem. Lett. 2006, 16, 469-472; (Pubitemid 41680648)
    • (2006) Bioorganic and Medicinal Chemistry Letters , vol.16 , Issue.2 , pp. 469-472
    • Deng, W.1    Guo, Z.2    Guo, Y.3    Feng, Z.4    Jiang, Y.5    Chu, F.6
  • 6
    • 37849049329 scopus 로고    scopus 로고
    • Designsynthesis, and multivariate quantitative structure- activity relationship of salicylanilides, potent inhibitors of type III secretion in Yersinia
    • (f) Dahlgren, M. K.; Kauppi, A. M.; Olsson, I. M.; Linusson, A.; Elofsson, M. Design, synthesis, and multivariate quantitative structure- activity relationship of salicylanilides, potent inhibitors of type III secretion in Yersinia. J. Med. Chem. 2007, 50, 6177;
    • (2007) J. Med. Chem. , vol.50 , pp. 6177
    • Dahlgren, M.K.1    Kauppi, A.M.2    Olsson, I.M.3    Linusson, A.4    Elofsson, M.5
  • 8
    • 65349142609 scopus 로고    scopus 로고
    • New antituberculotics originated from salicylanilides with promising in vitro activity against atypical mycobacterial strains
    • (h) Imramovský, A.; Vinsová, J.; Férriz, J. M.; Dolezal, R.; Jampílek, J.; Kaustová, J.; Kunc, F. New antituberculotics originated from salicylanilides with promising in vitro activity against atypical mycobacterial strains. Bioorg. Med. Chem. 2009, 17, 3572-3579;
    • (2009) Bioorg. Med. Chem. , vol.17 , pp. 3572-3579
    • Imramovský, A.1    Vinsová, J.2    Férriz, J.M.3    Dolezal, R.4    Jampílek, J.5    Kaustová, J.6    Kunc, F.7
  • 10
    • 0141742677 scopus 로고
    • Kinetics and mechanisms for the two-phase reaction between aqueous aniline and benzoyl chloride in chloroform, with and without pyridine catalysis
    • (a) Wamser, C. C.; Yates, J. A. Kinetics and mechanisms for the two-phase reaction between aqueous aniline and benzoyl chloride in chloroform, with and without pyridine catalysis. J. Org. Chem. 1989, 54, 150-154;
    • (1989) J. Org. Chem. , vol.54 , pp. 150-154
    • Wamser, C.C.1    Yates, J.A.2
  • 11
    • 0033052839 scopus 로고    scopus 로고
    • Microwavepromoted trifluoroacetylation of amines with TiO(CF3CO2) 2
    • (b) Iranpoor, N.; Zeynizadeh, B. Microwavepromoted trifluoroacetylation of amines with TiO(CF3CO2)2. J. Chem. Res. 1999, 124-125;
    • (1999) J. Chem. Res. , pp. 124-125
    • Iranpoor, N.1    Zeynizadeh, B.2
  • 12
    • 0033588063 scopus 로고    scopus 로고
    • Solvent-free synthesis of amides from non-enolizable esters and amines using microwave irradiation
    • DOI 10.1016/S0040-4039(99)01209-5, PII S0040403999012095
    • (c) Varma, R. S.; Naicker, K. P. Solvent-free synthesis of amides from non-enolizable esters and amines using microwave irradiation. Tetrahedron Lett. 1999, 40, 6177-6180; (Pubitemid 29378405)
    • (1999) Tetrahedron Letters , vol.40 , Issue.34 , pp. 6177-6180
    • Varma, R.S.1    Naicker, K.P.2
  • 13
    • 0034696595 scopus 로고    scopus 로고
    • Thin layer chromatography as a tool for reaction optimisation in microwave assisted synthesis
    • (d) Williams, L. Thin-layer chromatography as a tool for reaction optimisation in microwave-assisted synthesis. Chem. Comm. 2000, 435-436; (Pubitemid 30169610)
    • (2000) Chemical Communications , Issue.6 , pp. 435-436
    • Williams, L.1
  • 14
    • 0034615967 scopus 로고    scopus 로고
    • Direct transacylation of 2,2,2-trihaloethyl esters with amines and alcohols using phosphorus(III) reagents for reductive fragmentation and in situ activation
    • DOI 10.1021/jo991711m
    • (e) Hans, J. J.; Driver, R. W.; Burke, S. D. Direct transacylation of 2,2,2-trihaloethyl esters with amines and alcohols using phosphorus(III) reagents for reductive fragmentation and in situ activation. J. Org. Chem. 2000, 65, 2114-2121; (Pubitemid 30193896)
    • (2000) Journal of Organic Chemistry , vol.65 , Issue.7 , pp. 2114-2121
    • Hans, J.J.1    Driver, R.W.2    Burke, S.D.3
  • 15
    • 0000656897 scopus 로고    scopus 로고
    • The selective reaction of primary amines with carbonyl imidazole-containing compounds: Selective amide and carbamate synthesis
    • (f) Rannard, S. P.; Davis, N. J. The selective reaction of primary amines with carbonyl imidazole-containing compounds: Selective amide and carbamate synthesis. Org. Lett. 2000, 2, 2117-2120;
    • (2000) Org. Lett. , vol.2 , pp. 2117-2120
    • Rannard, S.P.1    Davis, N.J.2
  • 16
    • 38349135460 scopus 로고    scopus 로고
    • Multicomponent approach to the synthesis of oxidized amides through nitrile hydrozirconation
    • (g) Wan, S. Y.; Green, M. E.; Park, J. H.; Floreancig, P. E. Multicomponent approach to the synthesis of oxidized amides through nitrile hydrozirconation. Org. Lett. 2007, 9, 5385-5388;
    • (2007) Org. Lett. , vol.9 , pp. 5385-5388
    • Wan, S.Y.1    Green, M.E.2    Park, J.H.3    Floreancig, P.E.4
  • 17
    • 54049141740 scopus 로고    scopus 로고
    • Magnesium nitride as a convenient source of ammonia: Preparation of primary amides
    • (h) Veitch, G. E.; Bridgwood, K. L.; Ley, S. V. Magnesium nitride as a convenient source of ammonia: Preparation of primary amides. Org. Lett. 2008, 10, 3623-3625.
    • (2008) Org. Lett. , vol.10 , pp. 3623-3625
    • Veitch, G.E.1    Bridgwood, K.L.2    Ley, S.V.3
  • 18
    • 41649107870 scopus 로고    scopus 로고
    • Direct oxidative amidation of aldehydes with anilines under mechanical milling conditions
    • DOI 10.1021/jo800075t
    • (a) Gao, J.; Wang, G. W. Direct oxidative amidation of aldehydes with anilines under mechanical milling conditions. J. Org. Chem. 2008, 73, 2955-2958; (Pubitemid 351483020)
    • (2008) Journal of Organic Chemistry , vol.73 , Issue.7 , pp. 2955-2958
    • Gao, J.1    Wang, G.-W.2
  • 19
    • 34548151822 scopus 로고    scopus 로고
    • Metal-free one-pot oxidative amination of aldehydes to amides
    • (b) Ekoue-Kovi, K.; Wolf, C. Metal-free one-pot oxidative amination of aldehydes to amides. Org. Lett. 2007, 9, 3429-3432.
    • (2007) Org. Lett. , vol.9 , pp. 3429-3432
    • Ekoue-Kovi, K.1    Wolf, C.2
  • 20
    • 45849137092 scopus 로고    scopus 로고
    • Azido-Schmidt reaction for the formation of amides, imides, and lactams from ketones in the presence of FeCl3
    • Yadav, J. S.; Subba Reddy, B. V.; Subba Reddy, U. V.; Praneeth, K. Azido-Schmidt reaction for the formation of amides, imides, and lactams from ketones in the presence of FeCl3. Tetrahedron Lett. 2008, 49, 4742-4745.
    • (2008) Tetrahedron Lett. , vol.49 , pp. 4742-4745
    • Yadav, J.S.1    Subba Reddy, B.V.2    Subba Reddy, U.V.3    Praneeth, K.4
  • 21
    • 0027303052 scopus 로고
    • The conversion of carboxylic acids to amides via tin(II) reagents
    • (a) Burnell-Curty, C.; Roskamp, E. J. The conversion of carboxylic acids to amides via tin(II) reagents. Tetrahedron Lett. 1993, 34, 5193-5196;
    • (1993) Tetrahedron Lett. , vol.34 , pp. 5193-5196
    • Burnell-Curty, C.1    Roskamp, E.J.2
  • 22
    • 0028962805 scopus 로고
    • The conversion of carboxylic acids into amides via NCS=triphenylphosphine
    • (b) Froyen, P. The conversion of carboxylic acids into amides via NCS=triphenylphosphine. Synth. Commun. 1995, 25, 959-968;
    • (1995) Synth. Commun. , vol.25 , pp. 959-968
    • Froyen, P.1
  • 23
    • 0001454942 scopus 로고
    • Studied on amino acids and peptides, X: HPLC-mediated test of 2,4-bis(4-methoxyphenyl)- 1 3 2,4-dithiadiphosphetane 2,4-disulfide as a racemization-free coupling reagent in peptide synthesis
    • (c) Thorsen, J. D.; Andersen, T. P.; Pedersen, U.; Yde, B.; Leweson, S. Studied on amino acids and peptides, X: HPLC-mediated test of 2,4-bis(4-methoxyphenyl)- 1,3,2,4-dithiadiphosphetane 2,4-disulfide as a racemization-free coupling reagent in peptide synthesis. Tetrahedron 1985, 41, 5633-5636;
    • (1985) Tetrahedron , vol.41 , pp. 5633-5636
    • Thorsen, J.D.1    Andersen, T.P.2    Pedersen, U.3    Yde, B.4    Leweson, S.5
  • 24
    • 0036532557 scopus 로고    scopus 로고
    • Activation of carboxylic acids as their active esters by means of tert-butyl 3-(3,4-dihydrobenzotriazine-4-on)yl carbonate
    • DOI 10.1016/S0040-4039(02)00324-6, PII S0040403902003246
    • (d) Basel, Y.; Hassner, A. Activation of carboxylic acids as their active esters by means of tert-butyl 3-(3,4-dihydrobenzotriazine- 4-on)yl carbonate. Tetrahedron Lett. 2002, 43, 2529-2533; (Pubitemid 34242721)
    • (2002) Tetrahedron Letters , vol.43 , Issue.14 , pp. 2529-2533
    • Basel, Y.1    Hassner, A.2
  • 25
    • 0034627384 scopus 로고    scopus 로고
    • Efficient synthesis of primary amides using 2-mercaptopyridone-1-oxide- based uranium salts
    • (e) Bailén, M. A.; Chinchilla, R.; Dodsworth, D. J.; Nájera, C. Efficient synthesis of primary amides using 2-mercaptopyridone-1-oxide-based uranium salts. Tetrahedron Lett. 2000, 41, 9809-9813;
    • (2000) Tetrahedron Lett. , vol.41 , pp. 9809-9813
    • Bailén, M.A.1    Chinchilla, R.2    Dodsworth, D.J.3    Nájera, C.4
  • 27
    • 0035804514 scopus 로고    scopus 로고
    • A novel method for the mild and selective amidation of diesters and the amidation of monoesters
    • DOI 10.1016/S0040-4039(01)00079-X, PII S004040390100079X
    • (g) Guo, Z.; Dowdy, E.; Li, W. S.; Polniaszek, R.; Delaney, E. A novel method for the mild and selective amidation of diesters and the amidation of monoesters. Tetrahedron Lett. 2001, 42, 1843-1845; (Pubitemid 32179550)
    • (2001) Tetrahedron Letters , vol.42 , Issue.10 , pp. 1843-1845
    • Guo, Z.1    Dowdy, E.D.2    Li, W.-S.3    Polniaszek, R.4    Delaney, E.5
  • 28
    • 34249943025 scopus 로고    scopus 로고
    • Parallel synthesis of an amide library based on the 6,8-dioxa-3- azabicyclo[3 2.1]octane scaffold by direct aminolysis of methyl esters
    • (h) Machetti, F.; Bucelli, I.; Kappe, C. O.; Guarna, A. Parallel synthesis of an amide library based on the 6,8-dioxa-3-azabicyclo[3. 2.1]octane scaffold by direct aminolysis of methyl esters. J. Comb. Chem. 2007, 9, 454-461.
    • (2007) J. Comb. Chem. , vol.9 , pp. 454-461
    • MacHetti, F.1    Bucelli, I.2    Kappe, C.O.3    Guarna, A.4
  • 29
    • 0037060989 scopus 로고    scopus 로고
    • Solvent-free preparation of amides from acids and primary amines under microwave irradiation
    • DOI 10.1016/S0040-4020(02)00085-6, PII S0040402002000856
    • (a) Perreux, L.; Loupy, A.; Volatron, F. Solvent-free preparation of amides from acids and primary amines under microwave irradiation. Tetrahedron 2002, 58, 2155-2162; (Pubitemid 34185529)
    • (2002) Tetrahedron , vol.58 , Issue.11 , pp. 2155-2162
    • Perreux, L.1    Loupy, A.2    Volatron, F.3
  • 30
    • 17844409344 scopus 로고    scopus 로고
    • An atom efficient and solvent-free synthesis of structurally diverse amides using microwaves
    • DOI 10.1016/j.tetlet.2005.03.146
    • (b) Gelens, E.; Smeets, L.; Sliedregt, L. A. J. M.;van Steen, B. J.; Kruse, C. G.; Leurs, R.; Orru, R. V. A. An atom-efficient and solvent-free synthesis of structurally diverse amides using microwaves. Tetrahedron Lett. 2005, 46, 3751-3754; (Pubitemid 40591593)
    • (2005) Tetrahedron Letters , vol.46 , Issue.21 , pp. 3751-3754
    • Gelens, E.1    Smeets, L.2    Sliedregt, L.A.J.M.3    Van Steen, B.J.4    Kruse, C.G.5    Leurs, R.6    Orru, R.V.A.7
  • 31
    • 27744592156 scopus 로고    scopus 로고
    • Efficient method for the direct preparation of amides from carboxylic acids using tosyl chloride under solvent-free conditions
    • DOI 10.1016/j.tetlet.2005.08.021
    • (c) Khalafi-Nezhad, A.; Parhami, A.; Rad, M. N. S.; Zarea, A. Efficient method for the direct preparation of amides from carboxylic acids using tosyl chloride under solvent-free conditions. Tetrahedron Lett. 2005, 46, 6879-6882; (Pubitemid 41583409)
    • (2005) Tetrahedron Letters , vol.46 , Issue.40 , pp. 6879-6882
    • Khalafi-Nezhad, A.1    Parhami, A.2    Soltani Rad, M.N.3    Zarea, A.4
  • 32
    • 15044344246 scopus 로고    scopus 로고
    • Microwave-assisted sequential amide bond formation and intramolecular amidation: A rapid entry to functionalized oxindoles
    • DOI 10.1021/ol0473804
    • (d) Poondra, R. R.; Turner, N. J. Microwave-assisted sequential amide bond formation and intramolecular amidation: A rapid entry to functionalized oxindoles. Org. Lett. 2005, 7, 863-866; (Pubitemid 40380245)
    • (2005) Organic Letters , vol.7 , Issue.5 , pp. 863-866
    • Poondra, R.R.1    Turner, N.J.2
  • 33
    • 41449108475 scopus 로고    scopus 로고
    • Microwave-assisted solvent-free synthesis of N-acetamides by amidation or aminolysis
    • (e) Ferroud, C.; Godart, M.; Ung, S.; Borderies, H.; Guy, A. Microwave-assisted solvent-free synthesis of N-acetamides by amidation or aminolysis. Tetrahedron Lett. 2008, 49, 3004-3008;
    • (2008) Tetrahedron Lett. , vol.49 , pp. 3004-3008
    • Ferroud, C.1    Godart, M.2    Ung, S.3    Borderies, H.4    Guy, A.5
  • 34
    • 84943002806 scopus 로고
    • Microwave-mediated synthesis of amide
    • (g) Vasquez-Tato, M. P. Microwave-mediated synthesis of amide. Synlett 1993, 506.
    • (1993) Synlett , vol.506
    • Vasquez-Tato, M.P.1
  • 35
    • 0001918986 scopus 로고
    • A re-examination of the reaction between phosphorus trichloride and salicylic acid
    • Richard, W. Y. A re-examination of the reaction between phosphorus trichloride and salicylic acid. J. Am. Chem. Soc. 1952, 74, 1672-1673.
    • (1952) J. Am. Chem. Soc. , vol.74 , pp. 1672-1673
    • Richard, W.Y.1
  • 36
    • 24344483855 scopus 로고    scopus 로고
    • Toward rapid, "green", predictable microwave-assisted synthesis
    • DOI 10.1021/ar040278m
    • (a) Roberts, B. A.; Strauss, C. R. Toward rapid, "green, "predictable microwave-assisted synthesis. Acc. Chem. Res. 2005, 38, 653-661; (Pubitemid 41260519)
    • (2005) Accounts of Chemical Research , vol.38 , Issue.8 , pp. 653-661
    • Roberts, B.A.1    Strauss, C.R.2
  • 37
    • 0035813244 scopus 로고    scopus 로고
    • Microwave-assisted organic synthesis-A review
    • (b) Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Microwave-assisted organic synthesis-A review. Tetrahedron 2001 57 9225-9283.
    • (2001) Tetrahedron , vol.57 , pp. 9225-9283
    • Lidström, P.1    Tierney, J.2    Wathey, B.3    Westman, J.4
  • 38
    • 0035742307 scopus 로고    scopus 로고
    • Reactivity and selectivity under microwaves in organic chemistry: Relation with medium effects and reaction mechanisms
    • (a) Loupy, A.; Perreux, L.; Liagre, M.; Burle, K.; Moneuse, M. Reactivity and selectivity under microwaves in organic chemistry: Relation with medium effects and reaction mechanisms. Pure Appl. Chem. 2001, 73, 161-166;
    • (2001) Pure Appl. Chem. , vol.73 , pp. 161-166
    • Loupy, A.1    Perreux, L.2    Liagre, M.3    Burle, K.4    Moneuse, M.5
  • 39
    • 0003155051 scopus 로고    scopus 로고
    • The rapid synthesis of organic compounds in microwave ovens
    • (b) Gedye, R. N.; Smith, F. E.; Westaway, K. C. The rapid synthesis of organic compounds in microwave ovens. Can. J. Chem. 1998, 66, 17-26.
    • (1998) Can. J. Chem. , vol.66 , pp. 17-26
    • Gedye, R.N.1    Smith, F.E.2    Westaway, K.C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.