Abstract
A simple one-pot method for a new Mannich-type reaction is reported. In this method a heteropoly acid is used as a catalyst for the synthesis of β-acetamido carbonyl compounds via a three-component reaction of an aldehyde, acetamide, and dimedone in acetonitrile at room temperature. This method offers several advantages such as good yields, simple procedure, low cost, and ease of workup.
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Zhu J, Bienayme H (2005) Multicomponent reactions. Wiley-VCH, Weinheim
Biginelli P (1893) Gazz Chim Ital 23:360
Biginelli P (1891) Ber 24:2962
Ugi I, Meyr R, Fetzer U (1959) Angew Chem 71:386
Ugi I, Steinbruckner C (1960) Angew Chem 72:267
Passerini M (1921) Gazz Chim Ital 51:181
Mannich C, Krosche W (1912) Arch Pharm 250:647
Mannich C (1917) Arch Pharm 255:261
Michael A, Bernhard W, Nikolaus R (1998) Angew Chem Int Ed 37:1400
Barluenga J, Viado AL, Aguilar E, Fustero S, Olano B (1993) J Org Chem 58:5972
Enders D, Moser M, Geibel G, Laufer MC (2004) Synthesis 2040
Mukhopadhyay M, Bhatia B, Iqbal J (1997) Tetrahedron Lett 38:1083
Rao IN, Prabhakaran EN, Das SK, Iqbal J (2003) J Org Chem 68:4079
Dahn U, Hagenmaier H, Hohne H, König WA, Wolf G, Zahner H (1997) Arch Microbiol 107:143
Tiwari AK, Kumbhare RM, Agawane SB, Ali AZ, Kumar KV (2008) Bioorg Med Chem Lett 18:4130
Dakin HD, West R (1928) J Biol Chem 78:745
Rao IN, Prabhakaran EN, Das SK, Iqbal J (2003) J Org Chem 68:4079
Bahulayan D, Das SK, Iqbal J (2003) J Org Chem 68:5735
Prabhakaran EN, Iqbal J (1999) J Org Chem 64:3339
Ghosh R, Maiti S, Chakraborty A, Chakraborty S (2006) Tetrahedron Lett 47:8137
Khodaei MM, Khosropour AR, Fattahpour P (2005) Tetrahedron 46:2105
Pandey G, Singh RP, Singh VK (2005) Tetrahedron Lett 46:2137
Tarek AS, Saad SE, Mohamed AI (2007) Tetrahedron Lett 48:6199
Das B, Reddy KR (2006) Helv Chim Acta 89:3109
Das B, Reddy KR, Ramu R, Thirupathi P, Ravikanth B (2006) Synlett 11:1756
Heravi MM, Ranjbar L, Derikvand F, Bamoharram FF (2007) Catal Commun 8:289
Rafiee E, Tork F, Joshaghani M (2006) Bioorg Med Chem Lett 16:1221
Maghsoodlou MT, Hassankhani A, Shaterian HR, Habibi SM, Mosaddegh E (2007) Tetrahedron Lett 48:1729
Nagarapu L, Bantu R, Puttireddy R (2007) Appl Catal A 332:304
Oskooie HA, Heravi MM, Tahershamsi L, Sadjadi S, Tajbakhsh M (2010) Synth Commun 40:1772
Fernandez AH, Alvarez RM, Abajo TM (1996) Synthesis 1299
Wan JP, Chai YF, Wu JM, Pan YJ (2008) Synlett 19:3068
Milenkovicl A, Fachel F, Faure R, Lemaire M (1999) Synth Commun 29:1535
Mao H, Wan J, Pan Y (2009) Tetrahedron 65:1026
Kozhevnikov IV (2002) Catalysts for fine chemical synthesis: catalysis by polyoxo metalates, vol 2. Wiley, Chichester
Heravi MM, Sadjadi S, Mokhtari Haj N, Oskooie HA, Bamoharram FF (2009) Catal Commun 10:1643
Heravi MM, Sadjadi S, Mokhtari Haj N, Oskooie HA, Hekmat Shoar R, Bamoharram FF (2009) Tetrahedron Lett 50:943
Heravi MM, Sadjadi S, Oskooie HA, Bamoharram FF (2009) Ultrason Sonochem 16:708
Bamoharram FF, Heravi MM, Roushani M, Toosi M, Jodeyre L (2009) Green Chem Lett Rev 2:35
Heravi MM, Sadjadi S, Oskooie HA, Hekmat Shoar R, Bamoharram FF (2009) Tetrahedron Lett 50:662
Heravi MM, Sadjadi S, Mokhtari Haj N, Oskooie HA, Hekmat Shoar R, Bamoharram FF (2009) Tetrahedron Lett 50:943
Heravi MM, Sadjadi S, Oskooie HA, Hekmat Shoar R, Bamoharram FF (2008) Catal Commun 9:470
Heravi MM, Bakhtiari K, Fatehi A, Bamoharram FF (2008) Catal Commun 9:289
Heravi MM, Alimadadi Jani B, Derikvand F, Bamoharram FF, Oskooie HA (2008) Catal Commun 10:272
Thampson BB (1968) J Pharm Sci 57:715
Bencovic SJ, Bencovic PA, Comfort DR (1969) J Am Chem Soc 91:1860
Anslyn EV, Dougherty DA (2006) Modern physical organic chemistry. University Science Books, Sausalito
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Javid, A., Heravi, M.M. & Bamoharram, F.F. One-pot three-component synthesis of β-acetamido carbonyl compounds catalyzed by heteropoly acids. Monatsh Chem 143, 831–834 (2012). https://doi.org/10.1007/s00706-011-0669-1
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DOI: https://doi.org/10.1007/s00706-011-0669-1