Summary.
Hantzsch 1,4-dihydropyridine compounds were synthesized efficiently in high yields at room temperature within short times in 1,1,3,3-N,N,N′,N′-tetramethylguanidinium trifluoroacetate as ionic liquid using ultrasound irradiation. The ionic liquid can be recovered conveniently and reused efficiently.
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References
a) Stout DM, Meyers AI (1982) Chem Rev 82: 223; b) Wei XY, Rulledge A, Triggle DJ (1989) J Mol Pharmacol 35: 541; c) Bossert F, Vater W (1989) Med Res Rev 9: 291
a) Janis RA, Triggle DJ (1983) J Med Chem 25: 775; b) Bocker RH, Guengerich FP (1986) J Med Chem 28: 1596
a) Gaudio AC, Korolkovas A, Takahata Y (1994) J Pharm Sci 83: 1110; b) Bossert F, Meyer H, Wehinger E (1981) Angew Chem Int Ed Engl 20: 762
a) Klusa V (1995) Drugs Fut 20: 135; b) Bretzel RG, Bollen CC, Maeser E, Federlin KF (1993) Am J Kidney Dis 21: 53; c) Bretzel RG, Bollen CC, Maeser E, Federlin KF (1992) Drugs Fut 17: 465; d) Boer R, Gekeler V (1995) Drugs Fut 20: 499
A Hantzsch (1882) Liebigs Ann Chem 215 1
a) Love B, Snader KM (1965) J Org Chem 30: 1914; b) Alajarin R, Vaquero JJ, Garcia JLN, Alvarez-Builla J (1992) Synlett 297
A Sausins G Duburs (1988) Heterocycles 27 269 Occurrence Handle1:CAS:528:DyaL1cXit1Wmsrw%3D
a) Gordeev MF, Patel DV, Gordon EM (1996) J Org Chem 61: 924; b) Breitenbucher JG, Figliozzi G (2000) Tetrahedron Lett 41: 4311; c) Ohberg L, Westman J (2001) Synlett 1296; d) Anderson AG, Berkelhammer G (1958) J Am Chem Soc 80: 992; e) Philips AP (1949) J Am Chem Soc 71: 4003; f) Maquestiau A, Maeyence A, Eynde JJV (1991) Tetrahedron Lett 32: 3839; g) Zolfigol MA, Safaiee M (2004) Synlett 827; h) Szemes F, Marchalin S, Pronayova N, Szemes F, Daich A (2003) Heterocycles 59: 779; i) Kidwai M, Saxena S, Mohan R, Venkataramanan R (2002) J Chem Soc Perkin Trans 1, 1845; j) Tewari N, Dwivedi N, Tripathi RP (2004) Tetrahedron Lett 45: 9011
a) Yadav JS, Reddy BVS, Basak AK, Narsaiah AV (2003) Green Chem 5: 60; b) Sabitha G, Reddy KK, Reddy CS, Yadav JS (2003) Tetrahedron Lett 44: 4129
a) Mason TJ (1997) Chem Soc Rev 26: 443; b) Cintas P, Luche JL (1999) Green Chem 1: 115
a) Kumar A (2001) Chem Rev 1: 101; b) Welton T (1999) Chem Rev 99: 2071; c) Wasserscheid P, Keim W (2000) Angew Chem Int Ed 39: 3772; d) Sheldon R (2001) Chem Commun 2399
R Schiff J Puliti (1883) Ber Atsch Chem Ges 16 1607
D Emmert E Diefenbach R Eck (1927) Ber Atsch Chem Ges 60 2220
Hinkel LE, Madel WR (1929) J Chem Soc 750
JS Yadav BVS Reddy PT Reddy (2001) Synth Commun 31 425 Occurrence Handle10.1081/SCC-100000534 Occurrence Handle1:CAS:528:DC%2BD3MXksFGhtr8%3D
WV Walther R Raetze (1902) J Prakt Chem 65 287
R Lepetit (1887) Ber Atsch Chem Ges 20 133
RA Cobum M Wierzba MJ Suto AJ Solo AM Triggle DJ Triggle (1988) J Med Chem 31 2103
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Shaabani, A., Rezayan, A., Rahmati, A. et al. Ultrasound-accelerated Synthesis of 1,4-Dihydropyridines in an Ionic Liquid. Monatsh. Chem. 137, 77–81 (2006). https://doi.org/10.1007/s00706-005-0405-9
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DOI: https://doi.org/10.1007/s00706-005-0405-9