[KSCI] Korea Science Citation Index Service

http://dx.doi.org/10.5012/bkcs.2011.32.11.3963

Rapid One-pot, Four Component Synthesis of Pyranopyrazoles Using Heteropolyacid Under Solvent-free Condition

Chavan, Hemant V. (Medicinal Chemistry Research Laboratory, School of Chemical Sciences, Solapur University)
Babar, Santosh B. (Medicinal Chemistry Research Laboratory, School of Chemical Sciences, Solapur University)
Hoval, Rahul U. (Medicinal Chemistry Research Laboratory, School of Chemical Sciences, Solapur University)
Bandgar, Babasaheb P. (Medicinal Chemistry Research Laboratory, School of Chemical Sciences, Solapur University)

Publication Information

Bulletin of the Korean Chemical Society / v.32, no.11, 2011 , pp. 3963-3966 More about this Journal

Abstract

A series of pyranopyrazoles, was efficiently synthesized via one-pot, four component reaction of ethyl acetoacetate, hydrazine hydrate, aldehydes and malononitrile in the presence of catalytic amount silicotungstic acid under solvent free condition. NOE experiments confirmed that the product exist exclusively in the 2H form. The present protocol offers the advantages of clean reaction, short reaction time, high yield, easy purification and economic availability of the catalyst.

Keywords

Pyranopyrazoles; Multicomponent; Heteropolyacid; Solvent-free; NOE;

Citations & Related Records

Times Cited By Web Of Science : 1 (Related Records In Web of Science)
Times Cited By SCOPUS : 1

Reference

1	Mecadon, H.; Rohman, Md. R.; Kharbangar, I.; Laloo, B. M.; Kharkongor, I.; Rajbangshi, M.; Myrboh, B. Tetrahedron Lett. 2011, 52, 3228. DOI ScienceOn
2	Bandgar, B. P.; Bettigeri, S. V.; Phopse, J. Org. Lett. 2004, 6, 2105. DOI ScienceOn
3	Bandgar, B. P.; Bandgar, S. B.; Korbad, B. L.; Sawant, S. S. Tetrahedron Lett. 2007, 48, 1287. DOI ScienceOn
4	Bandgar, B. P.; Korbad, B. L.; Patil, S. A.; Bandgar, S. B.; Chavan, H. V.; Hote, B. S. Aust. J. Chem. 2008, 61, 700. DOI ScienceOn
5	Bandgar, B. P.; Patil, S. A.; Korbad, B. L.; Bandgar, S. B.; Hote, B. S. Aust. J. Chem. 2008, 61, 552. DOI ScienceOn
6	Abdelrazek, F. M.; Metz, P.; Metwally, N. H.; El-Mahrouky, S. F. Arch. Pharm. 2006, 339, 456. DOI ScienceOn
7	Abdelrazek, F. M.; Metz, P.; Kataeva, O.; Jager, A.; EI-Mahrouky, S. F. Arch. Pharm. 2007, 340, 543. DOI ScienceOn
8	Foloppe, N.; Fisher, L. M.; Howes, R.; Potter, A.; Robertson, A. G. S.; Surgenor, A. E. Bioorg. Med. Chem. 2006, 14, 4792. DOI ScienceOn
9	Sosnovskikh, V. Y.; Barabanov, M. A.; Usachev, B. I.; Irgashev, R. A.; Moshkin, V. S. Russ. Chem. Bull., Int. Ed. 2005, 54, 2846.
10	El-Assiery, S. A.; Sayed, G. H.; Acta Pharm. 2004, 54, 143.
11	Guard, J. A. M.; Steel, P. J. ARKIVOC 2001, vii, 32.
12	Kamakshi, R.; Reddy, B. S. R. Catalysis Commun. 2007, 8, 825. DOI ScienceOn
13	Molnar, A.; Beregszaszi, T. Tetrahedron Lett. 1997, 37, 8597.
14	Beregzazi, T.; Torok, B.; Molnar, A.; Olah, G. A.; Prakash, G. K. S. Catalysis Lett. 1997, 48, 83. DOI
15	Molnar, A.; Keresszegi, C. S.; Beregszaszi, T.; Torok, B.; Bartok, M. Catalysis of Organic Reactions; Marcell Dekker: New York, 1998; p 507.
16	Heravi, M. M.; Sadjadi, S.; Oskooie, H. A.; Shoar, R. H.; Bamoharram, F. F. Tetrahedron Lett. 2009, 50, 662. DOI ScienceOn
17	Rafiee, E.; Shahbhazi, F. J. Mol. Cat A: Chemical. 2006, 250, 57. DOI ScienceOn
18	Rafiee, E.; Shahbhazi, F.; Joshaghani, M.; Tork, F. J. Mol. Cat A: Chemical. 2005, 242, 129. DOI ScienceOn
19	Wang, J. L.; Liu, D.; Zhang, Z. J.; Shan, S.; Han, X.; Srinivasula, S. M.; Croce, C. M.; Alnemri, E. S.; Huang, Z. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 7124. DOI
20	El-Tamany, E. S.; El-Shahed, F. A.; Mohamed, B. H. J. Serb. Chem. Soc. 1999, 64, 9.
21	Zaki, M. E. A.; Soliman, H. A.; Hiekal, O. A.; Rashad, A. E. Z. Naturforsch. C. 2006, 61c, 1.
22	Junek, H.; Aigner, H. Chem. Ber. 1973, 106, 914. DOI
23	Rodinovskaya, L. A.; Gromova, A. V.; Shestopalov, A. M.; Nesterov, V. N. Russ. Chem. Bull., Int. Ed. 2003, 52, 2207. DOI
24	Otto, H. H. Arch. Pharm. 1974, 307, 444.
25	Otto, H. H.; Schmelz, H. Arch. Pharm. 1979, 312, 478. DOI
26	Wamhoff, H.; Kroth, E.; Strauch, K. Synthesis 1993, 11, 1129.
27	Tacconi, G.; Gatti, G.; Desimoni, G. J. Prakt. Chem. 1980, 322, 831. DOI
28	Sharanin Yu, A.; Sharanina, L. G.; Puzanova, V. V. Zh. Org. Khim. 1983, 19, 2609.
29	Vasuki, G.; Kumaravel, K. Tetrahedron Letters 2008, 49, 5636. DOI ScienceOn
30	Kuppusamy, K.; Kasi, P. Tetrahedron Letters 2010, 51, 3312. DOI ScienceOn
31	Mecadon, H.; Rohman, Md. R.; Rajbangshi, M.; Myrboh, B. Tetrahedron Lett. 2011, 52, 2523. DOI ScienceOn
32	Kozhevnikov, I. V. Chem. Rev. 1998, 98, 171. DOI ScienceOn
33	Kozhevnikov, I. V.; Derouane, E., Eds., In Catalysis for Fine Chemical Synthesis, Catalysis by Polyoxometalates 2; Wiley: New York, 2002.
34	Romanelli, G. P.; Bennardi, D.; Ruiz, D. M.; Baronetti, G.; Thomas, H. J.; Autino, J. C. Tetrahedron Lett. 2004, 45, 8935.
35	Torok, B.; Bucsi, I.; Beregszaszi, T.; Kapocsi, I.; Molnar, A. J. Mol. Cat A: Chem. 1996, 107, 305. DOI ScienceOn
36	Torok, B.; Bucsi, I.; Beregszaszi, T.; Kapocsi, I.; Molnar, A. Catalysis of Organic Reactions; Marcel Dekker: New York, 1996; p 393.
37	Clark, J. H. Acc. Chem. Res. 2002, 35, 791. DOI ScienceOn

Reference

8	Hemant V. Chavan. (2013) ACS Sustainable Chemistry & Engineering Pods: An Efficient Surfactant Type Catalyst for Synthesis of 3-Carboxycoumarins and Cinnamic Acids via Knoevenagel Condensation / 1 (8) , 929
4	Keyume Ablajan. (2013) Molecular Diversity Cerium ammonium nitrate (CAN)-catalyzed four-component one-pot synthesis of multi-substituted pyrano[2,3- $$\varvec{c}$$ c ]pyrazoles under ultrasound irradiation / 17 (4) , 693
1537-744X	Harshita Sachdeva. (2013) The Scientific World Journal ZnO Nanoparticles as an Efficient, Heterogeneous, Reusable, and Ecofriendly Catalyst for Four-Component One-Pot Green Synthesis of Pyranopyrazole Derivatives in Water / 2013 (1537-744X) , 1
2090-9071	Sunil U. Tekale. (2013) Journal of Chemistry Nano-ZnO Catalyzed Green and Efficient One-Pot Four-Component Synthesis of Pyranopyrazoles / 2013 (2090-9071) , 1
12	Ahmad Reza Moosavi-Zare. (2013) New Journal of Chemistry Synthesis of 6-amino-4-(4-methoxyphenyl)-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazoles using disulfonic acid imidazolium chloroaluminate as a dual and heterogeneous catalyst / 37 (12) , 4089
5	G. Santhosh Kumar. (2013) Organic Preparations and Procedures International An Efficient Multi-component Synthesis of 6-Amino-3-methyl-4-Aryl-2,4- dihydropyrano[2,3-c]Pyrazole-5-carbonitriles / 45 (5) , 429
1	Majid M. Heravi. (2014) Journal of the Iranian Chemical Society Applications of heteropoly acids in multi-component reactions / 11 (1) , 209
6	Ashok Vishram Borhade. (2015) Journal of the Iranian Chemical Society ZnS nanoparticles as an efficient and reusable catalyst for synthesis of 4H-pyrano[2,3-c]pyrazoles / 12 (6) , 1107
91	Mohammad Abdollahi-Alibeik. (2015) RSC Adv. /MNPs): an efficient magnetically recyclable catalyst for the synthesis of 1,4-dihydropyrano[2,3-c]pyrazole derivatives / 5 (91) , 74932
3	Mohammad G. Dekamin. (2016) Journal of the Iranian Chemical Society An efficient catalyst- and solvent-free method for the synthesis of medicinally important dihydropyrano[2,3-c]pyrazole derivatives using ball milling technique / 13 (3) , 591
6	Mohammad Ali Zolfigol. (2016) Applied Organometallic Chemistry ]pyrazoles / 31 (6) , e3633
1	(2017) Reaction Kinetics, Mechanisms and Catalysis Synthesis of dihydropyrano[2,3-c]pyrazoles using Ca9.5Mg0.5(PO4)5.5(SiO4)0.5F1.5 as a new nano cooperative catalyst / 122 (1) , 229
12	Ramin Ghorbani-Vaghei. (2017) Applied Organometallic Chemistry nanoparticle-supported IL) as a novel, green and heterogeneous catalyst / 31 (12) , e3816
2	Mohammad Bakherad. (2017) Research on Chemical Intermediates Using magnetized water as a solvent for a green, catalyst-free, and efficient protocol for the synthesis of pyrano[2,3-c]pyrazoles and pyrano[4′,3′:5,6]pyrazolo [2,3-d]pyrimidines / 43 (2) , 1013
8	Surya Narayana Maddila. (2017) Research on Chemical Intermediates CeO2/ZrO2 as green catalyst for one-pot synthesis of new pyrano[2,3-c]-pyrazoles / 43 (8) , 4313
02682605	(2017) Applied Organometallic Chemistry as a new Schiff base complex and catalyst / (02682605) , e3968
1568-5675	(2018) Research on Chemical Intermediates Synergetic effects of naturally sourced metal oxides in organic synthesis: a greener approach for the synthesis of pyrano[2,3-c]pyrazoles and pyrazolyl-4H-chromenes / (1568-5675)
02682605	(2018) Applied Organometallic Chemistry MIL-53(Fe) Metal-Organic Frameworks (MOFs) as an Efficient and Reusable Catalyst for the One-Pot Four-Component Synthesis of Pyrano[2,3-c]-pyrazoles / (02682605) , e4679
12	Ebrahim Soleimani. (2015) Journal of the Chinese Chemical Society Synthesis of Pyranopyrazoles Using Magnetically Recyclable Heterogeneous Iron Oxide-silica Core-shell Nanocatalyst / 62 (12) , 1155
4	Sakharam B. Dongare. (2016) Journal of the Chinese Chemical Society ) Catalyzed Synthesis of Fused 7-Azaindole Derivatives Using Domino Knoevenagel-Michael Reaction / 63 (4) , 323
31	(2011) ChemistrySelect One‐Pot Multicomponent Synthesis of Pyrano[2,3 c]pyrazole Derivatives Using CMCSO <SUB>3</SUB> H as a Green Catalyst / 4 (31) , 9033
1945-5453	(2019) Organic Preparations and Procedures International -chromene / (1945-5453) , 1
1735-2428	(2019) Journal of the Iranian Chemical Society Design and development of a new functionalized cellulose-based magnetic nanocomposite: preparation, characterization, and catalytic application in the synthesis of diverse pyrano[2,3-c]pyrazole derivatives / (1735-2428)
48	Mohammad Ali Zolfigol. (2011) RSC advances Synthesis of pyranopyrazoles using isonicotinic acid as a dual and biological organocatalyst / 3 (48) , 25681
48	Mohammad Ali Zolfigol. (2011) RSC advances Synthesis of pyranopyrazoles using isonicotinic acid as a dual and biological organocatalyst / 3 (48) , 25681
4	Shivkumar S. Jalde. (2011) Synthesis and reactivity in inorganic, metal-organic, and nano-metal chemistry An Efficient Solvent-Free Synthesis of Naphthopyranopyrimidines Using Heteropolyacid as an Ecofriendly Catalyst / 44 (4) , 623
1	Mahendra A. Chaudhari. (2011) Cogent chemistry A highly efficient and sustainable synthesis of dihydropyrano[2,3-<I>c</I>]pyrazoles using polystyrene-supported p-toluenesulfonic acid as reusable catalyst / 1 (1) , 1063830
2	(2011) 대한화학회지 Synthesis and Antimicrobial Screening of Pyrimidine Annulated Dihydropyrano[2, 3-c]pyrazole Derivatives / 62 (2) , 87
10	(2020) Asian journal of chemistry A Brief Study on the Role of Silicotungstic Acid in Modern Organic Syntheses / 32 (10) , 2423
11	(2011) Heterocycles Synthesis of Some Novel Antimicrobial and Antioxidant Agents of Functionalized Pyrazolo[4',3':5,6]pyrano[3,2-d]- [1,2]azaphospholes and Pyrazolo[4',3':5,6]pyrano[2,3-d][1,3,2]diazaphosphinines / 100 (11) , 1902
1	(2011) Inorganic and nano-metal chemistry An expedient and eco-friendly approach for multicomponent synthesis of dihydropyrano[2,3-c]pyrazoles using nano-Al<SUB>2</SUB>O<SUB>3</SUB>/BF<SUB>3</SUB>/Fe<SUB>3</SUB>O<SUB>4</SUB> as reusable catal / 50 (1) , 16
5	(2011) Research on chemical intermediates Green synthesis of pyranopyrazoles via biocatalytic one-pot Knoevenagel condensation-Michael-type addition-heterocyclization cascade in non-aqueous media / 46 (5) , 2805
2	(2011) Polycyclic aromatic compounds A Review on the Recent Multicomponent Synthesis of Pyranopyrazoles / 41 (2) , 223