Synthesis of 1-alkyl triazolium triflate room temperature ionic liquids and their catalytic studies in multi-component Biginelli reaction
Proceedings of the Indian Academy of Sciences - Chemical Sciences - Tập 127 - Trang 1539-1545 - 2015
Tóm tắt
Synthesis of three Brnsted acid-based ionic liquids, namely, 1-ethyl-1,2,4-triazolium triflate (1a), 1-propyl-1,2,4-triazolium triflate (1b) and 1-butyl-1,2,4-triazolium triflate (1c), is described. These ionic liquids have been employed as catalysts for convenient and high-yielding one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones and 3,4-dihydropyrimidin-2(1H)-thiones, which are Biginelli reaction products. Advantages of the methodology are operational convenience, short reaction times, avoidance of chromatographic purification and non-production of toxic waste. Further, the catalysts are easily recovered and reused without any noticeable diminution in their catalytic activity.
Tài liệu tham khảo
Posner G H 1986 Chem. Rev. 86 831
Safari J and Ravandi S G 2014 J. Mol. Struct. 1065 241
Biginelli P 1893 Gazz. Chim. Ital. 23 360
Alvim H G O, Lima T B, Oliveira A L, Oliveira H C B, Silva F M, Gozzo F C, Souza R Y, Silva W A and Net B A D 2014 J. Org. Chem. 79 3383
Murata H Ishitani H and Iwamoto M 2010 Org. Biomol. Chem. 8 1202 and the references cited therein
Rudrawa S 2005 Synlett. 7 1197
Cepanec I, Litvic M, Bartolincic A and Lovric M 2005 Tetrahedron 61 4275
Adibi H, Samimi H A and Beygzadeh M 2007 Catal. Commun. 8 2119
Mondal J, Sen T and Bhaumik A 2012 Dalton Trans. 41 6173
Seyedi N 2013 Transition. Met. Chem. 38 93
Paraskar A S, Dewkar G K and Sudalai A 2003 Tetrahedron Lett. 44 3305
Reddy V Y, Kurva S and Tammishetti S 2004 Catal. Commun. 5 511
Bose D S, Fatima L and Mereyala M H B 2003 J. Org. Chem. 68 587
Khaleghi S, Heravi M M, Khosroshahi M, Behbahani F K and Daroogheha Z 2008 Green Chem. Lett. Rev. 2 133
Reddy C V, Mahesh M, Raju P V K, Babu T R and Reddy V V N 2002 Tetrahedron Lett. 43 2657
Ranu B C, Hajra A and Jana U 2000 J. Org. Chem. 65 6270
Antoniotti S 2003 Synlett 10 1566
Zhang H, Zhou Z, Yao Z, Xu F and Shen Q 2009 Tetrahedron Lett. 50 1622
Lannou M I, Helion F and Namy J L 2008 Synlett 1 105
Azizian J, Mohammadi A A, Karimi A R and Mohammadizadeh M R 2006 Applied Catal. A 300 85
Hashem S 2009 Synth. Commun. 39 958
Singh M O and Devi N S 2009 J. Org. Chem. 74 3141
Kumar K A, Kasthuraiah M, Reddy C S and Reddy C D 2001 Tetrahedron Lett. 42 7873
Safari J and Gandomi-Ravandi S 2014 New J. Chem. 38 3514
Zamani F and Izadi E 2013 Catal. Commun. 42 104
Mistry S R, Joshi R S, Sahoo S K and Maheria K C 2011 Catal. Lett. 141 1541
Rani V R, Srinivas N, Kishan M R, Kulkarni S J and Raghavan K V 2001 Green Chem. 3 305
Kang L, Jin D and Cai Y 2013 Synth. Commun. 43 1896
Narahari S R, Reguri B R, Gudaparthi O and Mukkanti K 2012 Tetrahedron Lett. 53 1543
Rajack A, Yuvaraju K, Praveen C and Murthy Y L N 2013 J. Mol. Catal. A 370 197
Ahmed N and Siddiqui Z N 2014 J. Mol. Catal. A 387 45
Kolvari E, Koukabi N and Armandpour O 2014 Tetrahedron 70 1383
Yuan C, Huang Z and Chen J 2012 Catal. Commun. 24 56
Safari J and Zarnegar Z 2014 New J. Chem. 38 358
Srivastava R 2010 Catal. Lett. 139 17
Hallett J P and Welton T 2011 Chem. Rev. 111 3508
Alvim H G O, de Lima T B, de Oliveira H C B, Gozzo F C, de Macedo J L, Abdelnur P V, Silva W A and Neto B A D 2013 ACS Catal. 3 1420
Dadhania A N, Patel V K and Raval D K 2012 J. Chem. Sci. 124 921
Shaabani A and Rahmati A 2005 Catal. Lett. 100 177
Chavan S S, Sharma Y O and Degani M S 2009 Green Chem. Lett. Rev. 2 175
Sharma N, Sharma U K, Kumar R and Richa Sinha A K 2012 RSC Adv. 2 10648
Hajipour A R, Khazdooz L and Zarei A 2011 Synth. Commun. 41 2200
Daily L A and Miller K M 2013 J. Org. Chem. 78 4196
Siddiqui I R, Srivastava A, Shamim S, Srivastava A, Waseem M A, Rahila S, Abumhdi A H, Srivastava A and Rai P 2014 J. Mol. Catal. A 382 126
Roy S R, Jadhavar P S, Seth K, Sharma K K and Chakraborti A K 2011 Synthesis 14 2261
Elango K, Srirambalaji R and Anantharaman G 2007 Tetrahedron Lett. 48 9059
Nagarajan S and Elango K 2014 Catal. Lett. 144 1507
Liu Q, Pan N, Xu J, Zhang W and Kong F 2013 Synth. Commun. 43 139
Ramalingan C and Kwak Y 2008 Tetrahedron 64 5023
Heravi M M, Derikvand F and Bamoharram F F 2005 J. Mol. Catal. A 242 173
Litvic M, Vecenaj I, Ladisic Z M, Lovric M, Vinkovic V and Litvic M F 2010 Tetrahedron 66 3463
Wanmei L 2011 Heterocycles 83 2067
Mukhopadhyay C and Datta A 2010 J. Heterocycl. Chem. 47 136
Pore M D 2007 Aust. J. Chem. 60 435
Misra A K, Agnihotri G and Madhusudan S K 2004 Indian J. Chem. B 43 2018
Aridoss G and Jeong Y T 2010 Bull Korean Chem. Soc. 31 863