A Novel Microwave-Assisted, One-Pot Three Component Synthesis Based Upon Environmentally Protection Principles
محورهای موضوعی : Micro & Nano Mechanicsکوروش متولی 1 , Zahra Yaghoubi 2
1 -
2 - IT Department, South Tehran Branch,Islamic Azad University, Tehran, Iran
کلید واژه: Three-component reaction, Pyridine, Microwave-assisted reaction, Solvent-free, fluid, synthesis,
چکیده مقاله :
In this research, a new synthesis method of 2-phenylH-imidaze(1,2-a] pyridines is, obtained ¡ from a one-pot, three-component reaction between pyridine, urea (or guanidine) and a-bromoketones under microwave irradiation by observing the obvious principles of fluid mechanics and solvent-free conditions in excellent yields. One-pot multicomponent reactions have been disclosed as an effective instrument for atom economic and fluid mechanics obvious synthesis principles with regards to their convergence, productivity, and generation of highly diverse and complex products from easily available starting materials.
Green chemistry in relationship with fluid mechanics obvious principles emphasizes the importance for environmentally clean and safe synthesis, which contains high atom efficiency, elimination of dangerous chemicals, and easy separation with recovery and reuse of chemicals. In this way, the utility of microwave energy in synthetic organic chemistry has been increasingly recognized as compared with conventional heating. Reactions promoted by microwave irradiation (MWI) have shown an environmentally friendly nature, greater selectivity, and enhanced reaction rate. Therefore, the MWI-mediated multicomponent reaction has erected a specific attractive synthetic strategy for the fast and efficient library generation.
1.Ugi I, Dombling A and Werner B, J Heterocycl Chem., 2000, 37, 647; Bienayme H, Hulme C, Oddon G and Schmitt P, Chem Eur J., 2000, 6, 3221; Zhu J, Bienayme H, Multicomponent Reactions; Wiley-VCH: Wein- heim, 2005.
2. Sheldon J, Mol Catal A, 1996, 107, 75.
3. Loupy A, Microwaves in Organic Synthesis; Wiley-VCH: Meinheim, Germany, 2002,
147; Varma R S, Green Chem., 1999, 1, 43; Kappe C O, Angew Chem Int Ed., 2004, 43,
6250; Lidstrom P, Tierney J and Wathey B, Tetrahedron, 2001, 57, 9225.
4. Katritzky A R, Xu Y J and Tu H, J Org Chem., 2003, 68, 4935.
5. Rival Y, Grassy G and Michel G, Chem Pharm Bull., 1992, 40, 1170.
6. Fisher M H and Lusi A, J Med Chem., 1972, 15, 982; Rival Y, Grassy G, Taudou A
and Ecalle R, Eur J Med Chem., 1991, 26, 13.
7. Hamdouchi C, Blas J de, Prado M del, Gruber J, Heinz B A, Vance L, J Med Chem.,
1999, 42, 50; Lhassani M, Chavignon O, Chezal J M, Teulade J C, Chapat J P, Snoeck
R, Andrei G, Balzarini J, Clercq E de and Gueier A, Eur J Med Chem., 1999, 34, 271.
8. Kaminsky J J and Doweyko A M, J Med Chem., 1999, 40, 427.
9. Rupert K C, Henry J R, Dodd J H, Wadsworth S A, Cavender D E, Olini G C, Fahmy
31 Journal of Mechanical Research and Application (JMRA), Vol. 14 No.3, 1403 (2024),24-31
B and Siekierka J, J Bioorg Med Chem Lett., 2003, 13, 347.
10. Hamdouchi C, Zhong B, Mendoza J, Collins E, Jaramillo C, Diego J E de, Robertson D, Spencer C D, Anderson B D, Watkins S A, Zhanga F and Brooks H B, Bioorg Med Chem Lett., 2005, 15, 1943.
11. Sanfilippo P J, Urbanski M, Press J B, Dubinsky B and Moore J B, J Med Chem., 1991,
34, 2060.
12. Goodacre S C, Street L J, Hallett D J, Crawforth J M, Kelly S, Owens A P, Blackaby W P, Lewis R T, Stanley J, Smith A J, Ferris P, Sohal B, Cook S M, Pike A, Brown N, Waord K A, Marshall G, Castro J L and Atack J R, J Med Chem., 2006, 49, 35.
13. Trapani G, Franco M, Ricciardi L, Latrofa A, Genchi G, Sanna E, Tuveri F, Cagetti E, Biggio G and Liso G, J Med Chem., 1997, 40, 3109.
14. Katritzky A R, Xu Y, Tu H, J Org Chem., 2003, 68, 4935.
15. Howard A S, Comprehensive Heterocyclic Chemistry II vol. 8, chapter 10 ed. by
Katritzky A R, Rees C W and Scriven E V F, Pergamon Press: London, 1996, pp. 262-274.
16. Liu Z, Chen Z C and Zheng Q G, Synth Commun., 2004, 34, 361.
17. Xie Y Y, Chen Z C and Zheng Q G, Synthesis, 2002, 1505.
18. Ueno M and Togo H, Synthesis, 2004, 2673.
19. Yadav J S, Reddy B V S, Rao Y G, Srinivas M and Narsaiah A V, Tetrahedron Lett.,
2007, 48, 7717.
20. Bakherad M, Nasr-Isfahani H, Keivanloo A and Doostmohammadi N, Tetrahedron
Lett., 2008, 49, 3819.
21. The experiments were performed using a microwave oven (ETHOS 1600, Milestone)
with a power of 600 W specially designed for organic synthesis.
22. Dong J Z, Jiu X C, Miao C L, Jin C D and Hua Y W, J Braz Chem Soc., 2009, 20(3),
482.
23. Ponnala S, Kumar S T V S K, Bhat B A and Sahu D P, Synth Commun., 2005, 35, 901.
24. Tomoda H, Hirano T, Saito S, Mutai T and Araki K, Bull Chem Soc Jpn., 1999, 72,
1327.
25. Mattu F and Marongiu E.,J.a.c.s,1998,7,12
