[KSCI] Korea Science Citation Index Service

http://dx.doi.org/10.5012/jkcs.2012.56.3.328

Ultrasound Mediated, Sodium Bisulfite Catalyzed, Solvent Free Synthesis of 6-Amino-3-methyl-4-substitued-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile

Darandale, Sunil N. (Department of Chemical Technology, Dr. Babasaheb Ambedkar Marathwada University)
Sangshetti, Jaiprakash N. (Department of Chemical Technology, Dr. Babasaheb Ambedkar Marathwada University)
Shinde, Devanand B. (Department of Chemical Technology, Dr. Babasaheb Ambedkar Marathwada University)

Publication Information

Journal of the Korean Chemical Society / v.56, no.3, 2012 , pp. 328-333 More about this Journal

Abstract

A simple, convenient and practical green synthetic protocol for sodium bisulfite catalyzed multicomponent reaction of ethyl acetoacetate, hydrazine hydrate, malononitrile, and various aldehydes for the synthesis of 6-amino-4-phenyl-3-methyl-2,4-ihydropyrano[2,3-c]pyrazole-5-carbonitriles using ultrasound irradiations in solvent free condition. This method provides the advantage of operational simplicity, shorter reaction time and excellent yields making the protocol environment friendly and economically lucrative.

Keywords

Pyrano[2,3-c]pyrazole; Substituted aldehydes; Sodium bisulfite catalyst;

Citations & Related Records

Reference

1	Sangshetti, J. N.; Kokare, N. D.; Kotharkar, S. A.; Shinde, D. B. Monatsh. Chem. 2008, 139, 125. DOI
2	Sangshetti, J. N.; Chabukswar, A. R.; Shinde, D. B. Bioorg. Med. Chem. Lett. 2011, 21, 444. DOI
3	Wang, S. X.; Li Z.Y.; Zhang, J. C.; Li, J. T. Ultrason. Sonochem. 2008, 15, 677. DOI
4	Ganem, B. Acc. Chem. Res. 2009, 42, 463. DOI ScienceOn
5	Sunderhaus, J. D.; Martin, S. F. Chem. Eur. J. 2009, 15, 1300. DOI
6	Satyanarayana, V, S.; Sivakumar, A. Ultrason. Sonochem. 2011, 18, 917. DOI
7	Mason, T. J. Chem. Soc. Rev. 1997, 26, 443. DOI
8	Foloppe, N.; Fisher, L. M.; Howes, R.; Potter, A.; Robertson, A. G.; Surgenor, A. E. Bioorg. Med. Chem. 2006, 14, 4792. DOI
9	Kuo, S. C.; Huang, L. J.; Nakamura, H. J. Med. Chem. 1984, 27, 539. DOI
10	Wang, J. L.; Liu, D.; Zheng, Z. J.; Shan, S.; Han, X.; Srinivasula, S. M.; Croce, C. M. Alnemri, E. S.; Huang, Z. Proc. Natl. Acad. Sci. 2000, 97, 7124. DOI
11	Zaki, M. E.; Soliman, H. A.; Hiekal, O. A.; Rashad, A. E. Naturforsch. 2006, 61, 1. DOI
12	Abdelrazek, F. M.; Metz, P.; Kataeva, O.; Jager, A.; El-Mahrouky, S. F. Arch. Pharm. 2007, 340, 543. DOI
13	El-Tamany, E. S.; El-Shahed, F. A.; Mohamed, B. H. J. Serb. Chem. Soc. 1999, 64, 9.
14	Al-Matar, H. M.; Khalil, K. D.; Adam, A. Y.; Elnagdi, M. H. Molecules 2010, 15, 6619. DOI
15	Peng, Y.; Song, G.; Dou, R. Green Chem. 2006, 8, 573. DOI
16	Vasuki, G.; Kumaravel, K. Tetrahedron Lett. 2008, 49, 5636. DOI
17	Kanagaraj, K.; Pitchumani, K. Tetrahedron Lett. 2010, 51, 3312. DOI
18	Mecadon, H.; Rohman, M. R.; Kharbangar, I.; Laloo, B. M.; Kharkongor, I.; Rajbangshi, M.; Myrboh B. Tetrahedron Lett. 2011, 52, 3228. DOI
19	Mecadon, H.; Rohman, M. R.; Rajbangshi, M.; Myrboh, B. Tetrahedron Lett. 2011, 52, 2523. DOI

Reference

4	Jaiprakash N. Sangshetti. (2015) Journal of Taibah University for Science Water-mediated oxalic acid catalysed one-pot synthesis of 2-(substituted phenyl) phthalazin-1(2H)-ones / 9 (4) , 548
1	J. N. Sangshetti. (2015) Russian Journal of Organic Chemistry One-pot three-component synthesis of 3-(α-aminobenzyl)-4-hydroxycoumarin derivatives using nanocrystalline TiO2 as reusable catalyst / 51 (1) , 69
6	Massimiliano Lupacchini. (2017) Tetrahedron Sonochemistry in non-conventional, green solvents or solvent-free reactions / 73 (6) , 609
9	Binoyargha Dam. (2015) Catalysis Letters Magnetically Recyclable Nano-FDP: A Novel, Efficient Nano-Organocatalyst for the One-Pot Multi-Component Synthesis of Pyran Derivatives in Water Under Ultrasound Irradiation / 145 (9) , 1808
15	Essam M. Hussein. (2014) Synthetic Communications Sonochemistry: Synthesis of Bioactive Heterocycles / 44 (15) , 2155
5	Masoumeh Gholami Dehbalaei. (2017) Research on Chemical Intermediates Choline chloride based thiourea catalyzed highly efficient, eco-friendly synthesis and anti-bacterial evaluation of some new 6-amino-4-aryl-2,4-dihydro-3-phenyl pyrano [2,3-c] pyrazole-5-carbonitrile derivatives / 43 (5) , 3035
	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 , 1
	Sunil U. Tekale. (2013) Journal of Chemistry Nano-ZnO Catalyzed Green and Efficient One-Pot Four-Component Synthesis of Pyranopyrazoles / 2013 , 1
36	Debora Pereira Araujo. (2015) RSC Adv. Efficient sodium bisulfite-catalyzed synthesis of benzothiazoles and their potential as ureases inhibitors / 5 (36) , 28814
19	Bhartendu Pati Tripathi. (2017) New J. Chem. A green and clean pathway: one pot, multicomponent, and visible light assisted synthesis of pyrano[2,3-c]pyrazoles under catalyst-free and solvent-free conditions / 41 (19) , 11148
4	Michail N. Elinson. (2015) Monatshefte für Chemie - Chemical Monthly Solvent-free and ‘on-water’ multicomponent assembling of aldehydes, 3-methyl-2-pyrazoline-5-one, and malononitrile: fast and efficient approach to medicinally relevant pyrano[2,3-c]pyrazole scaffold / 146 (4) , 631
3	Essam M. Hussein. (2014) Review Journal of Chemistry Sonochemistry: Synthesis of bioactive heterocycles / 4 (3) , 221
4	(2012) Organic preparations and procedures international Green Methods for the Synthesis of Pyrazoles: A Review / 53 (4) , 317
11	(2018) Synthetic Communications Synthesis of six- and seven-membered heterocycles under ultrasound irradiation / 48 (11) , 1235
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)
5	(2012) Mini-reviews in organic chemistry Synthesis of Five-Membered Heterocycles Containing Nitrogen Heteroatom Under Ultrasonic Irradiation / 16 (5) , 481
31	(2012) 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