PEG-mediated catalyst-free expeditious synthesis of polysubstituted anilines and benzenes via the reaction of malononitrile and β-ketoester derivatives in the presence of activated acetylenes

Combinatorial Chemistry and High Throughput Screening

Volumn 15, Issue 7, 2012, Pages 571-575

  Piltan, Mohammad ^a   Moradi, Loghman ^b   Salimi, Hiwa ^a   Zargoosh, Kiomars ^c   Zarei, Seyed Amir ^a  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

^b UNIVERSITY OF KURDISTAN   (Iran)

^c ISFAHAN UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

ketoester; Activated acetylenes; Functionalized anilines and benzenes; Malononitrile; PEG

Indexed keywords

ANILINE DERIVATIVE; BENZENE DERIVATIVE; BETA KETOESTER DERIVATIVE; ESTER DERIVATIVE; MACROGOL; MALONONITRILE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

ALKYNES; ANILINE COMPOUNDS; BENZENE; COMBINATORIAL CHEMISTRY TECHNIQUES; ESTERS; MOLECULAR STRUCTURE; NITRILES; POLYETHYLENE GLYCOLS;

EID: 84865351093     PISSN: 13862073     EISSN: 18755402     Source Type: Journal    
DOI: 10.2174/138620712801619195     Document Type: Article

References (23)

1. Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: Oxford, 1998.
2. Tanaka, K. Solvent-Free Organic Synthesis; Wiley-VCH, 2003.
3. Mikami, K. Green Reaction Media for Organic Synthesis, Wiley-VCH, 2003.
4. Grieco, P. A. Organic Synthesis in Water; Blackie Academic and Professional: London, 1998.
5. Vasudevan, V. N.; Rajender, S. V. Polyethylene glycol as a non-ionic liquid solvent for Michael addition reaction of amines to conjugated alkenes. Green Chem., 2001, 3, 146-148.
6. Chen, J.; Spear, S. K.; Huddleston, J. G.; Rogers, R. D. Polyethylene glycol and solutions of polyethylene glycol as green reaction media. Green Chem., 2005, 7, 64-82. (Pubitemid 40311508)
7. Gibson, M. S. The Chemistry of the Amino Group; Patai, S., Ed.; Wiley-Interscience: London, 1968; pp 37-77.
8. Banthorpe, D. V. The Chemistry of the Amino Group; Patai, S., Ed.; Wiley-Interscience: London, 1968; pp 585-667.
9. Zaltsgendler, I.; Leblanc, Y.; Bernstein, A. Synthesis of aromatic amines from electron-rich arenes and bis(2,2,2-trichloroethyl) azodicarboxylate. Tetrahedron Lett., 1993, 34, 2441-2444.
10. Mitchell, H.; Leblanc, Y. Amination of arenes with electron-deficient azodicarboxylates. J. Org. Chem., 1994, 59, 682-687.
11. Hartwig, J. F. Transition metal catalyzed synthesis of arylamines and aryl ethers from aryl halides and triflates: Scope and mechanism. Angew. Chem., Int. Ed., 1998, 37, 2047-2067.
12. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Rational development of practical catalysts for aromatic carbon-nitrogen bond formation. Acc. Chem. Res., 1998, 31, 805-818. (Pubitemid 128473631)
13. Lee, S.; Jorgensen, M.; Hartwig, J. F. Palladium-catalyzed synthesis of arylamines from aryl halides and lithium bis(trimethylsilyl)amide as an ammonia equivalent. Org. Lett., 2001, 3, 2729-2732. (Pubitemid 33625283)
14. Shi, L.; Wang, M.; Fan, C.-A.; Zhang, F.-M.; Tu, Y.-Q. Rapid and efficient microwave-assisted amination of electron-rich aryl halides without a transition-metal catalyst. Org. Lett., 2003, 5, 3515-3517. (Pubitemid 37487451)
15. a) Fox, M. A.; Chanon, M. Eds. Photoinduced Electron Transfer; Elsevier: Amsterdam, 1988. b) Kurreck, H.; Huber M. Model reactions for photosynthesis-photoinduced charge and energy-transfer between covalently-linked porphyrin and quinone units. Angew. Chem., Int. Ed. Engl., 1995, 34, 849-866.
16. a) Prasad, P. N.; Williams, D. J. Introduction to Nonlinear Optical Effects in Molecules and Polymers; Wiley: New York, 1991. (b) Nalwa, H. S. Organic materials for third-order nonlinear optics. Adv. Mater., 1993, 5, 341-358. (c) Long, N. J. Organometallic compounds for nonlinear optics. - The search for En- light-enment! Angew. Chem., Int. Ed. Engl., 1995, 34, 21-38. (d) Wong, M. S.; Bosshard, C.; Pan, F.; Günter, P. Non-classical donor-acceptor chromophores for second order nonlinear optics. Adv. Mater., 1996, 8, 677-680.
17. a) Metzger, R. M.; Panetta, C. The quest for unimolecular devices New. J. Chem., 1991, 15, 209-221. (b) Launay J. P. Molecular Electronics. In Granular Nanoelectronics; Ferry, D. K., Ed.; Plenum Press: New York, 1991. (c) Petty, M. C.; Bryce, M. R.; Bloor, D. Eds. Introduction to Molecular Electronics; Oxford University Press: New York, 1995.
18. Banerjee, S.; Horn, A.; Khatri, H.; Sereda, G. A green one-pot multicomponent synthesis of 4H-pyrans and polysubstituted aniline derivatives of biological, pharmacological, and optical applications using silica nanoparticles as reusable catalyst. Tetrahedron Lett., 2011, 52, 1878-1881.
19. Yavari, I.; Moradi, L.; Mokhtarporyani-Sanandaj, A.; Mirzaei, A. You have full text access to this content Efficient Synthesis of Trialkyl 3-Phenylbuta-1,3-diene-1,2,4-tricarboxylates by a Novel One-Pot Multicomponent Reaction. Helv. Chim. Acta., 2007, 90, 392-394. (Pubitemid 46931575)
20. Yavari, I.; Mokhtarporyani-Sanandaj, A.; Moradi, L. An efficient synthesis of a new class of spiroheterocycles: diastereoselective synthesis of dihydropyrrolo[2,1-a]isoquinolines. Tetrahedron Lett., 2007, 48, 6709-6712. (Pubitemid 47284252)
21. Yavari, I.; Mirzaei, A.; Moradi, L. Efficient synthesis of dialkyl (2Z)-2-[(E)-1-aryl-2-(3-arylquinoxalin-2-yl)ethenyl]but-2-enedioates. Helv. Chim. Acta., 2006, 89, 2825-2829.
22. Yavari, I.; Piltan, M.; Moradi, L. Synthesis of pyrrolo[2,1-a] isoquinolines from activated acetylenes, benzoylnitromethanes, and isoquinoline. Tetrahedron, 2009, 65, 2067-2071.
23. Yavari, I.; Mirzaei, A.; Moradi, L.; Hosseini, N. Stereoselective synthesis of dialkyl 3-spiroindanedione-1,2,3,3a-tetrahydropyrrolo [1,2-a]quinoline-1,2-dicarboxylates. Tetrahedron Lett., 2008, 49, 2355-2358.