Imino Diels-Alder reactions: Efficient synthesis of pyrano and furoquinolines catalyzed by ZrCl4

Synthetic Communications

Volumn 34, Issue 22, 2004, Pages 4089-4104

  Mahesh, M ^a   Venkateshwar Reddy, Ch ^a   Srinivasa Reddy, K ^a   Raju, P V K ^a   Narayana Reddy, V V ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

2,3 dihydrofuran; 3,4 dihydro 2H pyran; Imino Diels Alder reaction; N benzylideneaniline; Zirconium tetrachloride

Indexed keywords

2,3 DIHYDROFURAN; 3,4 DIHYDRO 2H PYRAN; BENZYLIDENE DERIVATIVE; FURAN DERIVATIVE; IMINO ACID; PYRAN DERIVATIVE; UNCLASSIFIED DRUG; ZIRCONIUM DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIELS ALDER REACTION; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 8644238117     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200036586     Document Type: Article

References (18)

1. (a) Nesterova, I.N.; Alekseeva, L.M.; Andreeva, L.M.; Andreeva, N.I.; Golovira, S.M.; Granic, V.G. Synthesis and pharmocological activity of derivatives of 5-(dimethylamino) pyrano [3,2-c] quinoline-2-ones. Khim. Farm. Zh. 1995, 29 (2), 31(Russ).
2. Yamada, N.; Kadowaki, S.; Takahashi, K.; Umezu, K. MY-1250, a major metabolite of the antiallergic drug repirinast induces phosphorylation of a 78-Kda protein in rat mast cells. Biochem. Pharmacol. 1992, 44, 1211.
3. Faber, K.; Stueckler, H.; Kappe, T. Non-steroidal antiinflamatory agents. 1. Synthesis of 4-hydroxy-2-oxo-1,2-dihydroquinolin-3-ylalkanoic acids by the Wittig reaction of quinistatins. J. Heterocycle. Chem. 1984, 21 (4), 1177.
4. (a) Akhmed khodzhaeva, Kh.S.; Bessonova, I.A. Some data on the reaction between chemical structure and estrogenic activity in a series of quinoline alkaloids. Dokl. Akad. Nauk Uzb. SSR 1982 (9), 34(Russ).
5. Povarov, L.S. α,β-Unsaturated ethers and their analogues in reactions of Diene synthesis. Russ. Chem. Rev. 1967, 36, 656.
6. (a) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Yetterbium(III) triflate catalysed synthesis of quinoline derivatives from N-arylaldimines and vinyl ethers. Synthesis 1995, 801;
7. 3 catalysed three component coupling reaction between aldehyde, amine and diene or alkenes. Efficient synthesis of pyridine and quinoline derivatives. Chem. Lett. 1995, 6, 423.
8. (a) Kametani, T.; Takeda, H.; Suzuki, Y.; Honda, T. Synthesis of quinoline derivatives by [4 + 2] cycloaddition reaction. Synth. Commun. 1985, 15, 499;
9. (b) Lucchi, V.; Prato, M.; Scrrano, G.; Tecilla, P. Cycloaddition reactions of α-keto imines. Regio- and stereoselctivities in the dienic and dienophilic additions to conjugated dienes. J. Org. Chem. 1988, 35, 2251.
10. Ma, Y.; Qian, C.; Xie, M.; Sun, J. Lanthanide chloride catalyzed imino Diels-Alder reaction. One pot synthesis of pyrano [3,2-c] and furo [3,2-c] quinolines. J. Org. Chem. 1999, 64, 6462.
11. Babu, G.; Perumal, P.T. Convenient synthesis of pyrano [3,2-c] quinolines and Indeno[2,1-c]quinolines by Imino Diels-Alder reactions. Tetrahedron Lett. 1998, 39, 3225.
12. Yadav, J.S.; Subba Reddy, B.V.; Srinivas, R.; Madhuri, Ch.; Ramalingam, T. Lithium perchlorate/diethylether catalyzed Aza-Diels-Alder reaction: An expeditious synthesis of pyrano, indeno quinolines and phenanthridines. Synlett. 2001, 2, 240.
13. Boger, D.L. Heterodiene additions. In Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., eds.; Pergamon Press: Oxford, 1991; Vol. 5. 451.
14. Lewis, R.J.S.R. Dangerous Properties of Industrial Materials. Vol. 3, 7th ed.; Van Nostrand Reinhold: New York, 1989.
15. 3 as a Friedal-Crafts catalyst. J. Am. Chem. Soc. 1946, 68, 524.
16. Poll, T.; Helmchen, G.; Baue, B. Influence of polar groups in thermal and Lewis acid promoted asymmetric Diels-Alder additions. Lactic acid derivatives as practical highly selective and configurationally dichotomic reagents. Tetrahedron Lett. 1984, 25, 2191.
17. Evans, D.A.; Capman, K.T.; Bisaha, J. Asymmetric Diels-Alder cycloaddition reactions with chiral α,β-unsaturated- N-acyloxazolidinones. Am. Chem. Soc. 1988, 110, 1238.
18. Reddy, Ch.; Mahesh, M.; Raju, P.V.K.; Babu, T.R.; Reddy, V.V.N. Zirconium(IV)chloride catalysed one-pot synthesis of 3,4-dihydropyrimidine-2 (1H)- ones. Tetrahedron Lett. 2002, 43, 2657.