ISSN

0974-4150 (Online)
0974-4169 (Print)


Author(s): Balaji Bathrinarayanan, Panduragan Baskaran, Rajasekar Perumal, Syed Sheik Mansoor

Email(s): mansoorcah@gmail.com

DOI: 10.52711/0974-4150.2023.00067   

Address: Balaji Bathrinarayanan, Panduragan Baskaran, Rajasekar Perumal, Syed Sheik Mansoor* Research Department of Chemistry, Bioactive Organic Molecule Synthetic Unit, C. Abdul Hakeem College (Autonomous), Melvisharam – 632 509 Affiliated to Thiruvalluvar University, Vellore, Tamil Nadu, India. *Corresponding Author

Published In:   Volume - 16,      Issue - 6,     Year - 2023


ABSTRACT:
A simple approach for the one-pot multicomponent synthesis of 4-aryl-4,5-dihydro-1H-indeno[1,2-b]pyridines is described via the condensation of 1,3-indanedione, ß-ketoesters, ammonium acetate and various aromatic aldehydes in the presence of Chitosan as an environmentally benign eco-friendly catalyst. Furthermore, excellent yields, solvent-free condition, easy work-up protocol, reusability of the catalyst and mild reaction conditions are the advantages of this method.


Cite this article:
Balaji Bathrinarayanan, Panduragan Baskaran, Rajasekar Perumal, Syed Sheik Mansoor. Chitosan: An Efficient and Eco‐friendly catalyst for one-pot multicomponent access to dihydro-1H-indeno[1,2-b] pyridines. Asian Journal of Research in Chemistry. 2023; 16(6):412-6. doi: 10.52711/0974-4150.2023.00067

Cite(Electronic):
Balaji Bathrinarayanan, Panduragan Baskaran, Rajasekar Perumal, Syed Sheik Mansoor. Chitosan: An Efficient and Eco‐friendly catalyst for one-pot multicomponent access to dihydro-1H-indeno[1,2-b] pyridines. Asian Journal of Research in Chemistry. 2023; 16(6):412-6. doi: 10.52711/0974-4150.2023.00067   Available on: https://www.ajrconline.org/AbstractView.aspx?PID=2023-16-6-3


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.    Dömling A. Chem. Rev., Recent Developments in Isocyanide Based Multicomponent Reactions in Applied Chemistry. 2006; 106: 17-89.
4.    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
5.    Miri R. Javidnia K. Hemmateenejad B. Azarpira A. Amirghofran Z. Synthesis, cytotoxicity, QSAR, and intercalation study of new diindenopyridine derivatives. Bioorg Med Chem. 2004; 12, 2529–2536.
6.    Kunstmann R. Fischer G. Molecular analysis of hexahydro-1H-indeno[1,2-b]pyridines: potential antidepressants. J Med Chem., 1984; 27: 1312-1316.
7.    Augstein J. Ham AL. Leeming PR. Relation between antihistamine and antidepressant activity in hexahydroindenopyridines. J Med Chem. 1972; 15: 466-470.
8.    Bhusari KP, Amnerkar ND, Khedekar PB, Kale MK, Bhole RP. Synthesis and In Vitro Antimicrobial Activity of Some New 4-Amino-N-(1,3-Benzothiazol-2-yl) benzene sulphonamide derivatives. Asian J. Research Chem. 2008; 1(2): 53-58.
9.    Suha K. Al-Mosawi, Hanan A. Al-Hazam, Abbas F. Abbas. Synthesis, Characterization and Biological Study of Some Chalcones derived from Terphthaldehyde. Asian J. Research Chem. 2019; 12(3):153-156.
10.    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.
11.    Sudhan PN. Ghashang M. Mansoor SS. Tribromo melamine-catalyzed one-pot synthesis of a series of 4-aryl-4,5-dihydro-1H-indeno[1,2-b]pyridine derivatives. J Taibah Univ Sci. 2016; 10: 709–717.
12.    Samai S. Nandi GC. Kumar R. Singh MS. Multicomponent one-pot solvent-free synthesis of functionalized unsymmetrical dihydro-1H-indeno [1, 2-b] pyridines. Tetrahedron Lett. 2009; 50: 7096-7098.
13.    Mukhopadhyay C. Tapaswi PK. Butcher R.J. L-proline catalysed one-pot expeditious synthesis of highly substituted pyridines at room temperature Tetrahedron Lett. 2010; 51: 1797-1802.
14.    Khaksar S. Gholami M. An eco-benign and highly efficient access to dihydro-1H-indeno[1,2-b]pyridine in 2,2,2-trifluoroethanol. J Mol Liq. 2014; 196: 159-162.
15.    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
16.    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.
17.    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.
18.    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
19.    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
20.    Sato H. Ohtani H. Tsuge S. Characterization of chitin-based polymer hybrids by temperature-programmed analytical pyrolysis techniques. 2. Chitin-graft -poly(2-methyl-2-oxazoline)/Poly(vinyl alcohol) blends. Macromolecules. 2000; 33: 357-362
21.    Fan Y. Saito T. Isogai A. Individual chitin nano-whiskers prepared from partially deacetylated α-chitin by fibril surface cationization. Carbohydr. Polym. 2010; 79: 1046–1051.
22.    Tony J. Liu T. Lam E. Moores A. Chitin and chitosan on the nanoscale. Nanoscale Horiz. 2021; 6, 505-542.
23.    Nardo TD. Hadad C. Nhien ANV. Moores A. Synthesis of high molecular weight chitosan from chitin by mechanochemistry and aging. Green Chem. 2019; 21: 3276–3285.
24.    Kadib AE. Chitosan as a sustainable organocatalyst: a concise overview. Chem Sus Chem. 2015; 8: 217- 244.
25.    McIlwee HA. Schauer CL. Praig VG. Boukherroub R. Szunerits S. Thin chitosan films as a platform for SPR sensing of ferric ions. Analyst. 2008; 133, 673.
26.    Barroso T. Roque ACA. Aguiar-Ricardo A. Bioinspired and sustainable chitosan-based monoliths for antibody capture and release. RSC Adv. 2012; 2: 11285.
27.    Kumar M. McGlade D. Lawler J. Functionalized chitosan derived novel positively charged organic–inorganic hybrid ultrafiltration membranes for protein separation. RSC Adv. 2014; 4, 21699.
28.    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: 127–133.
29.    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.
30.    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.
31.    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
32.    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.

Recomonded Articles:

Author(s): Prathima Patil, S.P. Sethy, T. Sameena, K. Shailaja

DOI:         Access: Open Access Read More

Author(s): Gullipilli Sandhya, R. Ravichandra Babu

DOI: 10.5958/0974-4150.2018.00115.3         Access: Open Access Read More

Author(s): Suha K. Al-Mosawi, Hanan A. Al-Hazam, Abbas F. Abbas

DOI: 10.5958/0974-4150.2019.00031.2         Access: Open Access Read More

Author(s): Kateryna Taran, Ayaou Abderrahim, Vera Kravchenko, Olena Novosel, Svitlana Taran

DOI: 10.5958/0974-4150.2020.00034.6         Access: Open Access Read More

Author(s): Arun Kumar, Vinita Gupta, Sanchita Singh, Y.K. Gupta

DOI: 10.5958/0974-4150.2017.00038.4         Access: Open Access Read More

Author(s): Mukund Nagarnaik, Arun Sarjoshi, Ajay Bodkhe, Bhupendra Khanal, Mayuri Pise, Girish Pandya

DOI: 10.5958/0974-4150.2015.00102.9         Access: Open Access Read More

Author(s): Ram C. Senwar, Krishna K. Rathore, Anita Mehta

DOI: 10.5958/0974-4150.2017.00022.0         Access: Open Access Read More

Author(s): Chavan Pooja Ajit, Avinash Mahadeo Bhagwat, Atul Prabhakar Chaudhari

DOI: 10.52711/0974-4150.2021.00061         Access: Open Access Read More

Author(s): P. Valentina, K. Ilango, Deepak Jain, Prerna Shukla

DOI:         Access: Open Access Read More

Author(s): Y. Padmavathi, Akari Anjali, Nayaka Raghavendra Babu, P Ravi Kumar

DOI: 10.5958/0974-4150.2017.00064.5         Access: Open Access Read More

Author(s): Virupakshi Prabhakar, Kondra Sudhakar Babu, L.K. Ravindranath, M. Sahanoor Basha, J. Latha

DOI: 10.5958/0974-4150.2017.00012.8         Access: Open Access Read More

Author(s): Tentu Nageswara Rao, Muralidhar Reddy Avuthu, B. Venkata Reddy, SNVS Murthy

DOI: 10.5958/0974-4150.2016.00076.6         Access: Open Access Read More

Author(s): Prasanna Reddy Battu, MS Reddy

DOI:         Access: Open Access Read More

Asian Journal of Research in Chemistry (AJRC) is an international, peer-reviewed journal devoted to pure and applied chemistry..... Read more >>>

RNI: Not Available                     
DOI: 10.5958/0974-4150 

Popular Articles


Recent Articles




Tags