Microwave assisted IMDAF# reaction: Microwave irradiation applied with success to cycloaddition reaction of N-propargyl-N-p-tolyl-N-2- furfurylamines

Molecular Diversity

Volumn 9, Issue 1-3, 2005, Pages 229-231

  Mance, Ana Dunja ^a   Jakopčić, Krešimir ^a  

^a UNIVERSITY OF ZAGREB   (Croatia)

Author keywords

Alkynylarylfurfurylamine; Epoxyisoindoline; IMDAF ; MAOS ; 4+2 cycloaddition

Indexed keywords

FURFURAL;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CYCLOADDITION; DIELS ALDER REACTION; HEAT TREATMENT; MICROWAVE IRRADIATION; PRIORITY JOURNAL; REACTION ANALYSIS; SUBSTITUTION REACTION; THERMOSTABILITY;

EID: 15444380334     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11030-005-3434-8     Document Type: Article

References (23)

1. Carruthers, W. Cycloaddition Reactions in Organic Synthesis, Pergamon Press, Oxford, 1990., and references cited therein.
2. Hayes, B.L., Microwave Synthesis: Chemistry at the Speed of Light, CEM Publishing, Matthews, 2002., and references cited therein; Loupy, A. (Ed), Wiley-VCH, 2002.
3. de la Hoz, A., Diaz-Ortis, A., Moreno A., and Langa, F., Cycloadditions under Microwave Irradiation Conditions: Methods and Applications, Eur. J. Org. Chem. (2000) 1308-1320.
4. Bilović, D., Stojanac, Ž. and Hahn, V., A Novel Type of Intramolecular Diels-Alder Reaction in the Furan Series, Tetrahedron Lett. ( 1964) 2071-2074. Bilović, D. and Hahn, V., On the Preparation of Some Tertiary Amines Containing the 2-Furfuryl Group. Isomerization of Allylaryl-(2-furfuryl)-amines to N-Aryl-4H-5,7a-Epoxyisoindolines, Croat. Chem. Acta. 39 (1967) 189-197.
5. Bilović, D., Stojanac, Ž. and Hahn, V., A Novel Type of Intramolecular Diels-Alder Reaction in the Furan Series, Tetrahedron Lett. ( 1964) 2071-2074. Bilović, D. and Hahn, V., On the Preparation of Some Tertiary Amines Containing the 2-Furfuryl Group. Isomerization of Allylaryl-(2-furfuryl)-amines to N-Aryl-4H-5,7a-Epoxyisoindolines, Croat. Chem. Acta. 39 (1967) 189-197.
6. Klepo, Ž. and Jakopčić, K., The influence of Substituents on the Rate of the Intramolecular Diels-Alder Reaction of Allyl aryl(2-furfuryl)amines, Croat. Chem. Acta. 47 (1975) 45-50. Klepo, Ž. and Jakopčić, K., Studies in the Furan Series. 23. Preparation of some New 5-Substituted furfurylallylarylamines. Influence of Substituents on the Intramolecular Diels-Alder (IMDA) Reaction, J. Heterocyclic Chem., 24 (1987) 1787-1791.
7. Klepo, Ž. and Jakopčić, K., The influence of Substituents on the Rate of the Intramolecular Diels-Alder Reaction of Allyl aryl(2-furfuryl)amines, Croat. Chem. Acta. 47 (1975) 45-50. Klepo, Ž. and Jakopčić, K., Studies in the Furan Series. 23. Preparation of some New 5-Substituted furfurylallylarylamines. Influence of Substituents on the Intramolecular Diels-Alder (IMDA) Reaction, J. Heterocyclic Chem., 24 (1987) 1787-1791.
8. Mance, A.D. and Jakopčić, K., The Intramolecular Diels-Alder Reaction of N-Aryl-cyclohexenyl-(2-furfuryl)-amines. The New Rout to Benzo[c, d]isoindole Derivative, Vestn. Slov. Kem. Društva. 33 (1986) 287-294. Mance, A.D., Jakopčić, K. and Šindler-Kulyk, M., New Substituted Alkenyl-Furfuryl-Aryl Amines: Synthesis and their Characterization, Synthetic Commun. 26 (1996) 923-933. Mance, A.D., Šindler-Kulyk, M., Jakopčić, K., Hergold-Brundi, A. and Nagl, A., New Epoxyisoindolines by Intramolecular Diels-Alder Reaction of some Methyl-substituted Allylaryl-2-furfurylamines, J. Heterocyclic Chem., 34 (1997) 1315-1322. Mance, A.D., Borovička, B., Karaman, B. and Jakopčić, K., New Synthesis of Substituted Isoindolines from Furans via Epoxyisoindolines, J. Heterocyclic Chem., 36 (1999) 1337-1341. Mance, A.D., Borovička, B. and Jakopčić, K., New Compounds in Ring-opening Reaction of 5-Substituted Epoxyisoindolines, J. Heterocyclic Chem. 39 (2002) 277-285.
9. Mance, A.D. and Jakopčić, K., The Intramolecular Diels-Alder Reaction of N-Aryl-cyclohexenyl-(2-furfuryl)-amines. The New Rout to Benzo[c, d]isoindole Derivative, Vestn. Slov. Kem. Društva. 33 (1986) 287-294. Mance, A.D., Jakopčić, K. and Šindler-Kulyk, M., New Substituted Alkenyl-Furfuryl-Aryl Amines: Synthesis and their Characterization, Synthetic Commun. 26 (1996) 923-933. Mance, A.D., Šindler-Kulyk, M., Jakopčić, K., Hergold-Brundi, A. and Nagl, A., New Epoxyisoindolines by Intramolecular Diels-Alder Reaction of some Methyl-substituted Allylaryl-2-furfurylamines, J. Heterocyclic Chem., 34 (1997) 1315-1322. Mance, A.D., Borovička, B., Karaman, B. and Jakopčić, K., New Synthesis of Substituted Isoindolines from Furans via Epoxyisoindolines, J. Heterocyclic Chem., 36 (1999) 1337-1341. Mance, A.D., Borovička, B. and Jakopčić, K., New Compounds in Ring-opening Reaction of 5-Substituted Epoxyisoindolines, J. Heterocyclic Chem. 39 (2002) 277-285.
10. Mance, A.D. and Jakopčić, K., The Intramolecular Diels-Alder Reaction of N-Aryl-cyclohexenyl-(2-furfuryl)-amines. The New Rout to Benzo[c, d]isoindole Derivative, Vestn. Slov. Kem. Društva. 33 (1986) 287-294. Mance, A.D., Jakopčić, K. and Šindler-Kulyk, M., New Substituted Alkenyl-Furfuryl-Aryl Amines: Synthesis and their Characterization, Synthetic Commun. 26 (1996) 923-933. Mance, A.D., Šindler-Kulyk, M., Jakopčić, K., Hergold-Brundi, A. and Nagl, A., New Epoxyisoindolines by Intramolecular Diels-Alder Reaction of some Methyl-substituted Allylaryl-2-furfurylamines, J. Heterocyclic Chem., 34 (1997) 1315-1322. Mance, A.D., Borovička, B., Karaman, B. and Jakopčić, K., New Synthesis of Substituted Isoindolines from Furans via Epoxyisoindolines, J. Heterocyclic Chem., 36 (1999) 1337-1341. Mance, A.D., Borovička, B. and Jakopčić, K., New Compounds in Ring-opening Reaction of 5-Substituted Epoxyisoindolines, J. Heterocyclic Chem. 39 (2002) 277-285.
11. Mance, A.D. and Jakopčić, K., The Intramolecular Diels-Alder Reaction of N-Aryl-cyclohexenyl-(2-furfuryl)-amines. The New Rout to Benzo[c, d]isoindole Derivative, Vestn. Slov. Kem. Društva. 33 (1986) 287-294. Mance, A.D., Jakopčić, K. and Šindler-Kulyk, M., New Substituted Alkenyl-Furfuryl-Aryl Amines: Synthesis and their Characterization, Synthetic Commun. 26 (1996) 923-933. Mance, A.D., Šindler-Kulyk, M., Jakopčić, K., Hergold-Brundi, A. and Nagl, A., New Epoxyisoindolines by Intramolecular Diels-Alder Reaction of some Methyl-substituted Allylaryl-2-furfurylamines, J. Heterocyclic Chem., 34 (1997) 1315-1322. Mance, A.D., Borovička, B., Karaman, B. and Jakopčić, K., New Synthesis of Substituted Isoindolines from Furans via Epoxyisoindolines, J. Heterocyclic Chem., 36 (1999) 1337-1341. Mance, A.D., Borovička, B. and Jakopčić, K., New Compounds in Ring-opening Reaction of 5-Substituted Epoxyisoindolines, J. Heterocyclic Chem. 39 (2002) 277-285.
12. Mance, A.D. and Jakopčić, K., The Intramolecular Diels-Alder Reaction of N-Aryl-cyclohexenyl-(2-furfuryl)-amines. The New Rout to Benzo[c, d]isoindole Derivative, Vestn. Slov. Kem. Društva. 33 (1986) 287-294. Mance, A.D., Jakopčić, K. and Šindler-Kulyk, M., New Substituted Alkenyl-Furfuryl-Aryl Amines: Synthesis and their Characterization, Synthetic Commun. 26 (1996) 923-933. Mance, A.D., Šindler-Kulyk, M., Jakopčić, K., Hergold-Brundi, A. and Nagl, A., New Epoxyisoindolines by Intramolecular Diels-Alder Reaction of some Methyl-substituted Allylaryl-2-furfurylamines, J. Heterocyclic Chem., 34 (1997) 1315-1322. Mance, A.D., Borovička, B., Karaman, B. and Jakopčić, K., New Synthesis of Substituted Isoindolines from Furans via Epoxyisoindolines, J. Heterocyclic Chem., 36 (1999) 1337-1341. Mance, A.D., Borovička, B. and Jakopčić, K., New Compounds in Ring-opening Reaction of 5-Substituted Epoxyisoindolines, J. Heterocyclic Chem. 39 (2002) 277-285.
13. Kappe, C.O., Murphee, S.S. and Padwa, A., Synthetic Aplication of Furan Diels-Alder Chemistry, Tetrahedron, 53 (1997) 14179-14233, and references cited therein.
14. Sauer, J. and Sustmann, R., Mechanistic Aspects of Diels-Alder Reaction: A Critical Survey, Angew. Chem., Int. Ed. Engl., 19 (1980) 779-807.
15. Spreitzer, H. and Mustafa, S., Isoindole in der pharmazeutischen Forschung, Pharmazie in Unserer Zeit (1991) 83-87.
16. Padwa, A., Brodney, M.A., Liu, B., Satake, K. and Wu, T., A Cycloaddition Approach toward the Synthesys of Substituted Indolines and Tetrahydroisoquinolines, J. Org. Chem. (1999) 3595-3607 and references cited therein.
17. Lee, M., Moritomo, H. and Kanematsu, K., A New route to Isoindole Nucleus via Furan-Pyrrol Ring-Exchange, J. Chem. Soc. Chem. Commun. (1994) 1535.
18. Katritzky, A.R., Paluchowska, M.H. and Gallos, J.K., Intramolecular Diels-Alder Cyclization of N-Furfurylpropargylamines: A Novel General Synthesis of Isoindoles, J. Heterocyclic Chem., 26 (1989) 421-426.
19. Hunt, I.R, Rogers, C., Woo, S., Rauk, A. and Keay, B.A., Why Do Catalytic Quantities of Lewis Acid Generally Yield More Product Then 1.1 equi in the Intramolecular Diels-Alder Reaction with a Furan Diene? Competitive Complexation NMR Studies Provide an Ansver, J. Am. Chem. Soc., 117 (1995) 1049-1056.
20. Tagmazyan, K. Ts., Mkrtchyan, R.S. and Babayan, A.T., Studies of the Amino Compounds, Zh. Org. Khim., 10 (1974) 1642-1648.
21. Mance, A.D., Jakopčić, K. and Šindler-Kulyk, M., New Substituted Alkenyl-furfuryl-Aryl Amines: Synthesis and their Characterization, Synthetic Commun., 26 (1996) 923-933.
22. Hergold-Brundić, A., Pavlović, G., Mance, A.D. and Jakopčić, K., N-(4-Methylphenyl)-N-(5-nitro-2-furfuryl)-N-prop-2- ynylamine, Acta Cryst. (2000). C56, e520-e521.
23. Babayan, A.T., Tagmazyan, K. Ts., Ioffe, A.I., Mkrtchyan, R.S. and Torosyan, G.O., Doklady Akad. Nauk Arm, VIII (1974) 275-279.