Author(s):
Panduragan Baskaran, Balaji Bathrinarayanan, Rajasekar Perumal, Syed Sheik Mansoor
Email(s):
mansoorcah@gmail.com
DOI:
10.52711/0974-4150.2023.00072 
Address:
Panduragan Baskaran, Balaji Bathrinarayanan, Rajasekar Perumal, Syed Sheik Mansoor*
Research Department of Chemistry, Bioactive Organic Molecule Synthetic Unit,
C. Abdul Hakeem College (Autonomous), Melvisharam – 632509,
Affiliated to Thiruvalluvar University, Vellore, Tamil Nadu, India.
*Corresponding Author
Published In:
Volume - 16,
Issue - 6,
Year - 2023
ABSTRACT:
An efficient procedure for the synthesis of various 2-amino-3-cyano-6-methyl-4-aryl-4H-pyrans is reported. It has been found that Caffeine catalyse the condensation reaction of aromatic aldehydes, malononitrile and ethyl acetoacetate efficiently under EtOH-H2O (1:1) at reflux conditions. This approach provides many merits such as high yields of products, clean, simple work-up, waste free, mild reaction conditions and commercially available catalyst.
Cite this article:
Panduragan Baskaran, Balaji Bathrinarayanan, Rajasekar Perumal, Syed Sheik Mansoor. Caffeine: An efficient and Reusable catalyst for the multicomponent synthesis of 2-amino-3-cyano-6-methyl-4-aryl-4H-pyrans. Asian Journal of Research in Chemistry. 2023; 16(6):438-2. doi: 10.52711/0974-4150.2023.00072
Cite(Electronic):
Panduragan Baskaran, Balaji Bathrinarayanan, Rajasekar Perumal, Syed Sheik Mansoor. Caffeine: An efficient and Reusable catalyst for the multicomponent synthesis of 2-amino-3-cyano-6-methyl-4-aryl-4H-pyrans. Asian Journal of Research in Chemistry. 2023; 16(6):438-2. doi: 10.52711/0974-4150.2023.00072 Available on: https://www.ajrconline.org/AbstractView.aspx?PID=2023-16-6-8
REFERENCES:
1. Ugi I. Recent progress in the chemistry of multicomponent reactions. Pure Appl Chem. 2001; 73: 187
2. Karthic R. Andrews B. Subramani K. Microwave assisted synthesis and antifungal studies of 5-amino thiadiazole substituted pyrimidine compounds. Asian J. Research Chem. 2017; 10(2): 119-123.
3. Tajudeen SS. Geetha K. Synthetic, crystal and In vitro antimicrobial studies of Compounds derived from pyrazinamide and nicotinohydrazide via a one-pot two components reaction. Asian J. Research Chem. 2017; 10(1):19-25
4. Ram C. Senwar, Krishna K. Rathore, Mehta A. Synthesis and antimicrobial evaluation of Azetidinone derivatives of pyridine containing hydrazides. Asian J. Res. Chem. 2017; 10(2): 135-141
5. Prabhakar V. Babu KS. Ravindranath LK. Venkateswarlu B. Synthesis and Biological Activities of Novel Thieno [3, 2-d] Pyrimidine Derivatives. Asian J. Research Chem. 2017; 10(2): 206-216.
6. Patil SA. Wang J. Li XS. Chen JJ. Jones TS. Hosni-Ahmed A. Patil R. Seibel WL. Li W. Miller DD. New substituted 4H-chromenes as anticancer agents. Bioorg. Med. Chem. Lett. 2012; 22: 4458−4461.
7. Makawana JA. Patel MP. Patel RG. Synthesis and antimicrobial evaluation of new pyrano [4,3-b]pyran and pyrano[3,2-c]chromene derivatives bearing a 2-thiophenoxyquinoline nucleus. Arch. Pharm. 2012; 345: 314−322.
8. Saundane AR. Vijaykumar K. Vaijinath AV. Synthesis of novel 2-amino-4-(5′-substituted-2′-phenyl-1H-indol-3′-yl)-6-aryl-4H- pyran-3-carbonitrile derivatives as antimicrobial and antioxidant agents. Bioorg. Med. Chem. Lett. 2013; 23: 1978−1984.
9. Venkatesham A. Rao RS. Nagaiah K. Yadav JS. Roopa Jones G. Basha S J. Sridhar B. Addlagatta A. Synthesis of new chromeno-annulated cis-fused pyrano[3,4-c]pyran derivatives via domino Knoevenagel-hetero-Diels-Alder reactions and their biological evaluation towards antiproliferative activity. Med Chem Comm 2012; 3: 652−658.
10. Kang SS. Cooper G. Dunne SF. Luan CH. Surmeier DJ. Silverman R B. Antagonism of L-type Ca2+ channels Cav1.3 and Cav1.2 by 1,4-dihydropyrimidines and 4H-pyrans as dihydropyridine mimics. Bioorg. Med. Chem. 2013; 21: 4365−4373.
11. Hafez EA. Elnagdi MH. Elagamey AA. El-Taweel FA. Nitriles in heterocyclic synthesis: novel synthesis of benzo[c]coumarin and of benzo[c]pyrano[3, 2-c]quinoline derivatives. Heterocycles. 1987; 26: 903-907.
12. Lei M. Ma L. Hu L. A green, efficient, and rapid procedure for the synthesis of 2-amino-3-cyano-1,4,5,6-tetrahydropyrano[3,2-c] quinolin-5-one derivatives catalyzed by ammonium acetate, Tetrahedron Lett. 2011; 52: 2597–600.
13. Ghashang M. Mansoor SS. Aswin K. Thiourea dioxide: an efficient and reusable organocatalyst for the rapid one-pot synthesis of pyrano[4,3-b]pyran derivatives in water. Chin. J. Catal. 2014; 35: 127–33.
14. Ghashang M. Mansoor SS. Mohammad Shafiee, M.R. Kargar M. Najafi Biregan M. Azimi F. Taghrir H. Green chemistry preparation of MgO nanopowders: efficient catalyst for the synthesis of thiochromeno[4, 3-b] pyran and thiopyrano[4, 3-b]pyran derivatives, J. Sulfur Chem. 2016 ; 37: 377–90.
15. Ghashang M. Mansoor SS. Shams Solaree L. Sharifian-Esfahani A. Multi-component, one-pot, aqueous media preparation of dihydropyrano[3, 2-c]chromene derivatives over MgO nanoplates as an efficient catalyst. Iran. J. Catal. 2016; 6 : 237–43.
16. Baziar A. Ghashang M. Preparation of pyrano [3, 2-c] chromene-3-arbonitriles using ZnO nano-particles: a comparison between the box–behnken experimental design and traditional optimization methods. Rean. Kinet. Mech. Catal. 2016; 118: 463–79.
17. Ghashang M. Kargar M. Shafiee MRM. Mansoor SS. Fazlinia A. Esfandiari H. CuO nano-structures prepared in rosmarinus officinalis leaves extract medium: efficient catalysts for the aqueous media preparation of dihydropyrano[3, 2-c]chromene derivatives. Recent Patents on Nanotechnology. 2015; 9: 204–211.
18. Nathanson, J. A. Caffeine and related mrthylxanthines: possible naturally occurring pesticides. Science. 1984; 226(4671): 184-187.
19. Mohebata R. Yazdani-Elah-Abadi A. Caffeine catalyzed green synthesis of novel benzo[a][1,3]oxazino[6,5-c] phenazines via a one-pot multi-component sequential protocol in a basic ionic liquid. Chin. Chem. Lett. 2017; 28: 1340–1344
20. Abadi AYE. Maghsoodlou MT. Heydari R. Mohebat R. An efficient four-component domino protocol for the rapid and green synthesis of functionalized benzo[a]pyrano[2,3-c]phenazine derivatives using caffeine as a homogeneous catalyst. Res Chem Intermed. 2016; 42: 1227–1235
21. Saghanezhad SJ. Caffeine-H2SO4: as an efficient bio-based catalyst for the one-pot preparation of 1,8-dioxo-octahydro xanthenes. Rev. Roum. Chim. 2018; 63(1): 67-72.
22. Gattouche S. Zenkhri, L. Belfar ML. Tabchouche A. Phytochemical Screening, Anti-Bacterial and Anti-oxidant Activities of some Aerial parts extracts in Atriplex halimus L., from Ouargla (Algeria). Asian J. Research Chem. 2020; 13(5): 365-372
23. Balgovind. Goshain O. Benzimidazole: A Promising target for the development of novel drug molecules against breast cancer. Asian J. Research Chem. 2023; 16(4): 303
24. Gupta, P. Yadav, HL. Garg, G. Pawar, RS. Patil, UK. Singour, PK. Synthesis and biological evaluation of some novel 2-aminobenzothiazole derivatives as potential analgesic agents. Asian J. Research Chem. 2010; 3(1):42-50
25. Boukraa N. Ladjel S. Goudjil MB. Eddoud A. Sanori. KWM. Chemical compositions, Fumigant and Repellent Activities, of Essential oils from three Indigenous medicinal plants and their mixture, against stored grain pest, Tribolium castaneum (Herbst) (Coleoptera: Tenebrionidae). Asian J. Research Chem. 2020; 13(6): 455-464.
26. Kishor Sonawane RK. Nere KR Mohite SK. Heterocyclic system containing bridgehead nitrogen atom: Substituted 1,2,3-Triazolo [3,4-b]-1,3,4-Thiadiazole derivative useful for the treatment of breast cancer and other diseases. Asian J. Research Chem. 2022; 15(4): 295-298.
27. Prabhakar V. Babu KS. Ravindranath LK. Venkateswarlu B. Synthesis and Biological Activities of Novel Thieno [3, 2-d] Pyrimidine Derivatives. Asian J. Research Chem. 2017; 10(2): 206-216.
28. Mansoor SS. Ariffin A. Sudhan SPN. Silica bonded N-propylpiperazine sodium n-propionate as an efficient recyclable catalyst for one-pot synthesis of 2-amino-4-aryl-4H,8H-6-methyl-8-oxopyrano[3,2-b]pyran Derivatives. Res. Chem. Intermed. 2015; 41(9): 6687–6705.
29. Ghashang M. Mansoor SS. Aswin K. Penta fluoro phenylammonium triflate (PFPAT) catalyzed facile construction of substituted chromeno[2,3-d]pyrimidinone derivatives and their antimicrobial activity. J. Adv. Res. 2014; 5: 209–218
30. Perumal R. Bathrinarayanan B. Ghashang M. Mansoor SS. An efficient one-Pot synthesis of 7,7-dimethyl-2-(2-oxo-2H-chromen-3-yl)-4-aryl-7,8-dihydroquinolin-5(6H)-one derivatives using Chitosan-SO3H as biodegradable organocatalyst. J. Heterocyclic Chem. 2019; 56(3): 947-955.
31. Aswin K. Mansoor SS. Logaiya K. Sudhan SPN. Triphenylphosphine: an efficient catalyst for the synthesis of 4,6-diphenyl-3,4-dihydropyrimidine-2(1H)-thione under thermal conditions. J. King Saud Univ - Sci. 2014; 26(2): 141-148.
32. Aswin K. Ghashang M. Mansoor S.S. An efficient synthesis of 4-aryl-7-benzylidene-hexahydro-2H-cyclopenta[d]pyrimidin-2-ones/thiones catalyzed by p-dodecylbenzene sulfonic acid. Iran. J. Catal. 2015; 5(2): 175-182.