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DOI: 10.1055/s-0030-1260067
Organocatalytic Application of Ionic Liquids: [bmim][MeSO4] as a Recyclable Organocatalyst in the Multicomponent Reaction for the Preparation of Dihydropyrimidinones and -thiones
Publikationsverlauf
Publikationsdatum:
10. Juni 2011 (online)
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Abstract
The organocatalytic potential of 1-butyl-3-methylimidazolium-based room-temperature ionic liquids has been investigated for the synthesis of dihydropyrimidinones and -thiones by a one-pot multicomponent reaction involving an aldehyde, a β-keto ester or β-diketone, and urea or thiourea in excellent yields in short time. Factors that influence the efficiency of the ionic liquid as a catalyst were examined such as the anion and the imidazolium cation, particularly the influence of C2 substitution in the latter. The ionic liquid can be recovered and reused for five consecutive reactions without significant loss of catalytic efficiency. The applicability of the methodology for large-scale reaction highlights its potential for bulk synthesis.
Key words
ionic liquid - organocatalyst - multicomponent reaction - dihydropyrimidinone - dihydropyrimidinethione
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1a
Dömling A. Chem. Rev. 2006, 106: 17 -
1b
Zhu J.Bienaymé H. Multicomponent Reactions Wiley-VCH; Weinheim: 2005. -
1c
Wipf P.Stephenson CRJ.Okumura K. J. Am. Chem. Soc. 2003, 125: 14694 - 2
Potosky J. Drug Discovery Today 2005, 10: 115 -
3a
Kappe CO. Molecules 1998, 3: 1 -
3b
Kappe CO. Eur. J. Med. Chem. 2000, 35: 1043 -
3c
Yarim M.Saraç S.Kiliç FS.Erol K. Farmaco 2003, 58: 17 -
3d
Kidwai M.Saxena S.Khan MKR.Thukral SS. Eur. J. Med. Chem. 2005, 40: 816 -
3e
Kumar P.Sankar BR.Nasir G.Baig RB.Chandrashekaran S. Eur. J. Med. Chem. 2009, 44: 4192 -
4a
Simon C.Constantieux T.Rodriguez J. Eur. J. Org. Chem. 2004, 4957 -
4b
Dallinger D.Stadler A.Kappe CO. Pure Appl. Chem. 2004, 76: 1017 -
4c
Kappe CO. Acc. Chem. Res. 2000, 33: 879 -
5a
Yangyun W.Jipan Y.Haohao Y.Zhiwei M.Ruyu C. Lett. Org. Chem. 2011, 8: 264 -
5b
Gore S.Baskaran S.Koenig B. Green Chem. 2011, 13: 1009 -
5c
Pani MS.Arjun M.Sridhar D.Srinivas K.Raviprasad T. Chin. Chem. Lett. 2009, 20: 909 -
5d
Shobha D.Chari MA.Ahn KH. Chin. Chem. Lett. 2009, 20: 1059 -
5e
Polshettiwar V.Varma RS. Tetrahedron Lett. 2007, 48: 7343 -
5f
Yu Y.Liu C.Luo G. Bioorg. Med. Chem. Lett. 2007, 17: 3508 -
5g
Mukhopadhyay C.Datta A.Banik BK. J. Heterocycl. Chem. 2007, 44: 979 -
5h
Bose AK.Manhas MS.Pednekar S.Ganguly SN.Dang H.He W.Mandadi A. Tetrahedron Lett. 2005, 46: 1901 -
5i
Tu S.Fang F.Miao C.Jiang H.Feng Y.Shi D.Wang X. Tetrahedron Lett. 2003, 44: 6153 -
5j
Shaabani A.Bazgir A.Teimouri F. Tetrahedron Lett. 2003, 44: 857 -
6a
Shen ZL.Xu XP.Ji SJ. J. Org. Chem. 2010, 75: 1162 -
6b
Tamaddon F.Razmi Z.Jafari AA. Tetrahedron Lett. 2010, 51: 1187 -
7a
Litvić M.Večenaj I.Ladišić ZM.Lovrić M.Vinković V.Litvić MF. Tetrahedron 2010, 66: 3463 -
7b
Sadek KU.Al-Qalaf F.Abdelkhalik MM.Elnagdi MH. J. Heterocycl. Chem. 2010, 47: 284 -
7c
Prodius D.Macaev F.Mereacre V.Shova S.Lutsenco Y.Styngach E.Ruiz P.Muraviev D.Lipkowski J.Simonov YA.Turta C. Inorg. Chem. Commun. 2009, 12: 642 -
7d
Chitra S.Pandiarajan K. Tetrahedron Lett. 2009, 50: 2222 -
7e
Lannou MI.Hélion F.Namy JL. Synlett 2008, 105 -
7f
Rodríguez-Domínguez JC.Bernardi D.Kirsch G. Tetrahedron Lett. 2007, 48: 5777 -
7g
Ahmed N.van Lier JE. Tetrahedron Lett. 2007, 48: 5407 -
7h
Cepanec I.Litvić M.Filipan-Litvić M.Grüngold I. Tetrahedron 2007, 63: 11822 -
7i
Suzuki I.Suzumura Y.Takeda K. Tetrahedron Lett. 2006, 47: 7861 -
7j
Cepanec I.Litvić M.Bartolinčić A.Lovrić M. Tetrahedron 2005, 61: 4275 -
7k
Su W.Li J.Zheng Z.Shen Y. Tetrahedron Lett. 2005, 46: 6037 -
7l
De S K.Gibbs RA. Synthesis 2005, 1748 -
7m
Wang Z.-T.Xu L.-W.Xia C.-G.Wang H.-Q. Tetrahedron Lett. 2004, 45: 7951 -
7n
Martins MAP.Teixeira MVM.Cunico W.Scapin E.Mayer R.Pereira CMP.Zanatta N.Bonacorso HG.Peppe C.Yuan Y.-F. Tetrahedron Lett. 2004, 45: 8991 -
7o
Paraskar AS.Dewkar GK.Sudalai A. Tetrahedron Lett. 2004, 44: 3305 -
7p
Bose DS.Fatima L.Mereyala HB. J. Org. Chem. 2003, 68: 587 -
7q
Sabitha G.Reddy GSKK.Reddy KB.Yadav JS. Tetrahedron Lett. 2003, 44: 6497 -
7r
Maiti G.Kundu P.Guin C. Tetrahedron Lett. 2003, 44: 2757 -
7s
Reddy CV.Mahesh M.Raju PVK.Babu TR.Reddy VVN. Tetrahedron Lett. 2002, 43: 2657 -
7t
Fu N.-Y.Yuan Y.-F.Cao Z.Wang S.-W.Wang J.-T.Peppe C. Tetrahedron 2002, 58: 4801 -
7u
Kumar KA.Kasthuraiah M.Reddy S.Reddy CD. Tetrahedron Lett. 2001, 42: 7873 -
7v
Dondoni A.Massi A.Sabbatini S. Tetrahedron Lett. 2001, 42: 4495 -
7w
Lu J.Bai Y.Wang Z.Yang B.Ma H. Tetrahedron Lett. 2000, 41: 9075 -
7x
Steele TG.Coburn CA.Patane MA.Bock MG. Tetrahedron Lett. 1998, 39: 9315 -
8a
Ramalingan C.Park S.-J.Lee I.-S.Kwak Y.-W. Tetrahedron 2010, 66: 2987 -
8b
Abdollahi-Alibeik M.Zaghaghi Z. Chem. Pap. 2009, 63: 97 -
8c
Suzuki I.Iwata Y.Takeda K. Tetrahedron Lett. 2008, 49: 3238 -
8d
Debache A.Amimour M.Belfaitah A.Rhouati S.Carboni B. Tetrahedron Lett. 2008, 49: 6119 -
8e
Azizian J.Mirza B.Mojtahedi MM.Abaee MS.Sargordan M. J. Fluorine Chem. 2008, 129: 1083 -
8f
Ryabukhin SV.Plaskon AS.Ostapchuk EN.Volochnyuk DM.Shishkin OV.Tolmachev AA. J. Fluorine Chem. 2008, 129: 625 -
8g
Zumpe FL.Flüß M.Schmitz K.Lender A. Tetrahedron Lett. 2007, 48: 1421 -
8h
Debache A.Boumoud B.Amimour M.Belfaitah A.Rhouati S.Carboni B. Tetrahedron Lett. 2006, 47: 5697 -
8i
Bose DS.Sudharshan M.Chavhan SW. ARKIVOC 2005, (iii): 228 ; http://www.arkat-usa.org/home -
8j
Bhosale RS.Bhosale SV.Bhosale SV.Wang T.Zubaidha PK. Tetrahedron Lett. 2004, 45: 9111 -
8k
Srinivas KVNS.Das B. Synthesis 2004, 2091 -
8l
Reddy KR.Reddy ChV.Mahesh M.Raju PVK.Reddy VVN. Tetrahedron Lett. 2003, 44: 8173 -
9a
Cheng Q.Wang Q.Xu X.Ruan M.Yao H.Yang X. J. Heterocycl. Chem. 2010, 47: 624 -
9b
Shobha D.Chari MA.Mano A.Selvan ST.Mukkanti K.Vinu A. Tetrahedron 2009, 65: 10608 -
9c
Shinde SV.Jadhav WN.Lande MK.Gadekar LS.Arbad BR.Kondre JM.Karade NN. Catal. Lett. 2008, 125: 57 -
9d
Zendehdel M.Mobinikhaledi A.Asgari A.
J. Inclusion Phenom. Macrocyclic Chem. 2008, 60: 353 -
9e
Mahdavinia GH.Sepehrian H. Chin. Chem. Lett. 2008, 19: 1435 -
9f
Lin HX.Zhao BX.Xu B.Wang XH. Chin. Chem. Lett. 2007, 18: 502 -
9g
Rafiee E.Jafari H. Bioorg. Med. Chem. Lett. 2006, 16: 2463 -
9h
Singh K.Arora D.Singh S. Tetrahedron Lett. 2006, 47: 4205 -
9i
Singh V.Sapehiyia V.Srivastava V.Kaur S. Catal. Commun. 2006, 7: 571 -
9j
Salehi P.Dabiri M.Zolfigol MA.Fard MAB. Tetrahedron Lett. 2003, 44: 2889 -
9k
Martínez S.Meseguer M.Casas L.Rodríguez E.Molins E.Moreno-Mañas M.Roig A.Sebastián RM.Vallribera A. Tetrahedron 2003, 59: 1553 -
9l
Bigi F.Carloni S.Frullanti B.Maggi R.Sartori G. Tetrahedron Lett. 1999, 40: 3465 -
10a
Pasunootia KK.Chaia H.Jensena CN.Gorityalaa BK.Wanga S.Liu X.-W. Tetrahedron Lett. 2011, 52: 80 -
10b
Niralwad KS.Sningate BB.Shingare MS. Tetrahedron Lett. 2010, 51: 3616 -
10c
Glasnova TN.Tyeb H.Kappe CO. Tetrahedron 2008, 64: 2035 -
10d
Banik BK.Reddy AT.Datta A.Mukhopadhyay C. Tetrahedron Lett. 2007, 48: 7392 -
10e
Manhas MS.Ganguly SN.Mukherjee S.Jain AK.Bose AK. Tetrahedron Lett. 2006, 47: 2423 -
10f
Kumar D.Sundaree MS.Mishra BG. Chem. Lett. 2006, 35: 1074 -
10g
Pasha MA.Swamy NR.Jayashankara VP. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2005, 44: 823 -
10h
Jenner G. Tetrahedron Lett. 2004, 45: 6195 -
10i
Bose AK.Pednekar S.Ganguly SN.Chakraborty G.Manhas MS. Tetrahedron Lett. 2004, 45: 8351 -
10j
Li JT.Han JF.Yang JH.Li TS. Ultrasound Sonochem. 2003, 10: 119 - 11
Tundo P.Anastas P.Black DS.Breen J.Collins T.Memoli S.Miyamoto J.Polyakoff M.Tumas W. Pure Appl. Chem. 2000, 72: 1207 - 12
Alfonsi K.Colberg J.Dunn PJ.Fevig T.Jennings S.Johnson TA.Kleine HP.Knight C.Nagy MA.Perry DA.Stefaniak M. Green Chem. 2008, 10: 31 - 13
Constable DJC.Gonzalez CJ.Henderson RK. Org. Process Res. Dev. 2007, 11: 133 -
14a
Organic Synthesis in Water
Grieco PA. Blackie Academic and Professional; London: 1998. -
14b
Li CJ.Chang TH. In Organic Reactions in Aqueous Media Wiley; New York: 1997. -
14c
Otto S.Engberts JBFN. Pure Appl. Chem. 2000, 72: 1365 -
14d
Ribe S.Wipf P. Chem. Commun. 2001, 299 -
14e
Engberts JBFN.Blandamer MJ. Chem. Commun. 2001, 1701 -
14f
Otto S.Engberts JBFN. Org. Biomol. Chem. 2003, 1: 2809 -
14g
Li C.-J. Chem. Rev. 2005, 105: 3095 -
14h
Narayan S.Muldoon J.Finn MG.Fokin VV.Kolb HC.Sharpless KB. Angew. Chem. Int. Ed. 2005, 44: 3275 -
14i
Li C.-J.Chen L. Chem. Soc. Rev. 2006, 35: 68 -
14j
Lindström UM.Andersson F. Angew. Chem. Int. Ed. 2006, 45: 548 -
14k
Chankeshwara SV.Chakraborti AK. Org. Lett. 2006, 8: 3259 -
14l
Khatik GL.Kumar R.Chakraborti AK. Org. Lett. 2006, 8: 2433 -
14m
Chakraborti AK.Rudrawar S.Jadhav KB.Kaur G.Chankeshwara SV. Green Chem. 2007, 9: 1335 -
14n
Hailes HC. Org. Process Res. Dev. 2007, 11: 114 -
14o
Organic
Reactions in Water
Lindström UM. Blackwell; Oxford: 2007. - 15
Sharma G.Kumar R.Chakraborti AK. Tetrahedron Lett. 2008, 49: 4269 ; and references therein - 16
Parikh N.Kumar D.Raha Roy S.Chakraborti AK. Chem. Commun. 2011, 47: 1797 - 17
Earle MJ.Sheldon RA. Pure Appl. Chem. 2000, 72: 1391 - 18
Isambert N.Duque MMS.Plaquevent JC.Rodriguez J.Constantieux T. Chem. Soc. Rev. 2011, 40: 1347 - 19
Dupont J.Spencer J. Angew. Chem. Int. Ed. 2004, 43: 5296 - 20
Ranke J.Stolte S.Störmann R.Arning J.Jastorff B. Chem. Rev. 2007, 107: 2183 - 21
Smiglak M.Reichert WM.Holbrey JD.Wilkes JS.Sun L.Thrasher JS.Kirichenko K.Singh S.Katritzky AR.Rogers RD. Chem. Commun. 2006, 2554 - 22
Costello DM.Brown LM.Lamberti GA. Green Chem. 2009, 11: 548 - 23
Coleman D.Gathergood N. Chem. Soc. Rev. 2010, 39: 600 - 24
de Maria PD. Angew. Chem. Int. Ed. 2008, 47: 6960 -
25a
Sarkar A.Raha Roy S.Chakraborti AK. Chem. Commun. 2011, 47: 4538 -
25b
Raha Roy S.Chakraborti AK. Org. Lett. 2010, 12: 3866 -
25c
Chakraborti AK.Raha Roy S. J. Am. Chem. Soc. 2009, 131: 6902 -
25d
Chakraborti AK.Raha Roy S.Kumar D.Chopra P. Green Chem. 2008, 10: 1111 -
26a
Legeay JC.Eynde JJV.Bazureau JP. Tetrahedron 2005, 61: 12386 -
26b
Legeay JC.Eynde JJV.Bazureau JP. Tetrahedron 2008, 64: 5328 -
27a
Arfan A.Paquin L.Bazureau JP. Russ. J. Org. Chem. 2007, 43: 1058 -
27b
Gholap AR.Venkatesan K.Thomas D.Lahoti RJ.Srinivasan KV. Green Chem. 2004, 6: 147 -
28a
Chen X.Peng Y. Catal. Lett. 2008, 122: 310 -
28b
Ahmad S.Abbas R. Catal. Lett. 2005, 100: 177 -
28c
Peng J.Deng Y. Tetrahedron Lett. 2001, 42: 5917 -
29a
Cho CW.Pham TPT.Jeon YC.Yun YS. Green Chem. 2008, 10: 67 -
29b
García-Lorenzo A.Tojo E.Tojo J.Teijeira M.Rodríguez-Berrocal FJ.González MP.Martínez-Zorzano VS. Green Chem. 2008, 10: 508 - 30
De Souza ROMA.da Penha ET.Milage HMS.Garden SJ.Esteves PM.Eberlin MN.Antunes OAC. Chem. Eur. J. 2009, 15: 9799 - 31
Mayer TU.Kapoor TM.Haggarty SJ.King RW.Schreiber SL.Mitchison TJ. Science 1999, 286: 971 - 32
Gartner M.Sunder-Plassmann N.Seiler J.Utz M.Vernos I.Surrey T.Giannis A. ChemBioChem 2005, 6: 1173