Microwave-assisted multicomponent synthesis of aza-, diaza-, benzo-, and dibenzofluorenedione derivatives

Synthetic Communications

Volumn 38, Issue 17, 2008, Pages 3003-3016

  Defant, Andrea ^a   Guella, Graziano ^a   Mancini, Ines ^a  

^a UNIVERSITY OF TRENTO   (Italy)

Author keywords

Heterocyclic cyclization; Microwave assisted synthesis; One pot synthesis; Regioselectivity

Indexed keywords

6,11 DIOXO 6,11 DIHYDRO BENZO[F]PYRIDO[1,2 A]INDOLE (2 DIMETHYLAMINO ETHYL) 12 CARBOXAMIDE; AMIDE; AMINE; ESTER DERIVATIVE; ETHYL 2 METHYL 5,10 DIOXO 5,10 DIHYDRO 4,6 DIAZABENZO[B]FLUORENE 11 CARBOXYLATE; ETHYL 2 METHYL 5,10 DIOXO 5,10 DIHYDRO 4,9A DIAZABENZO[B]FLUORENE 11 CARBOXYLATE; ETHYL 5,10 DIOXO 5,10 DIHYDRO 4,6 DIAZABENZO[B]FLUORENE 11 CARBOXYLATE; ETHYL 5,10 DIOXO 5,10 DIHYDRO 4,9A DIAZABENZO[B]FLUORENE 11 CARBOXYLATE; ETHYL 7,12 DIOXO 6B,7,12,12A TETRAHYDRO 6A,11 DIAZA DIBENZO[A,H]FLUORENE 13 CARBOXYLATE; ETHYL 7,12 DIOXO 6B,7,12,12A TETRAHYDRO 6A,8 DIAZA DIBENZO[A,H]FLUORENE 13 CARBOXYLATE; ETHYL 8,13 DIOXO 7A,8,13,13A TETRAHYDRO BENZO[5,6]INDOLO[2,1 A]ISOQUINOLINE 14 CARBOXYLATE; FLUORENE DERIVATIVE; HETEROCYCLIC COMPOUND; ISOQUINOLINE DERIVATIVE; METAL; POLYCYCLIC HYDROCARBON; PYRIDINIUM DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; BIOLOGICAL ACTIVITY; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; DRUG SYNTHESIS; HEATING; INTERMETHOD COMPARISON; ISOMERIZATION; MICROWAVE IRRADIATION; ONE POT SYNTHESIS; PRODUCTIVITY;

EID: 50649084307     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802044249     Document Type: Article

References (21)

1. (a) Lindrström, P.; Tierney, J.; Wathey, B.; Westman, J. Microwave assisted organic synthesis - A review. Tetrahedron 2001, 57, 9225-9283;
2. (b) Perreux, L.; Loupy, A. A tentative rationalization of microwave effects in organic synthesis according to the reaction medium, and mechanistic considerations. Tetrahedron 2001, 57, 9199-9223;
3. (c) Hayes, B. L. Recent advances in microwave-assisted synthesis. Aldrichim. Acta 2004, 37, 66-77;
4. (d) Caddick, S. Microwave assisted organic reactions. Tetrahedron 1995, 51, 10403-10432.
5. (a) Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathe, D. New solvent-free organic synthesis using microwaves. Synthesis 1998, 1213-1234;
6. (b) Varma, R. S. Solvent-free accelerated organic synthesis using microwaves. Pure Appl. Chem. 2001, 73, 193-198.
7. Varma, R. S. Solvent-free organic syntheses using supported reagents and microwave irradiation. Green Chem. 1999, 1, 43-55.
8. Alexandre, F.-R.; Domon, L.; Frère, S.; Testard, A.; Thiéry, V.; Bresson, T. Microwaves in drug discovery and multi-step synthesis. Mol. Div. 2003, 7, 273-280.
9. (a) Bagley, M. C.; Lubinu, M. C. Microwave-assisted multicomponent reactions for the synthesis of heterocycles. Top Heterocycl. Chem. 2006, 1, 31-58;
10. (b) El Ashry, E. H.; Kassem, A. A. Account of microwave irradiation for accelerating organic reactions. Arkivoc 2006, 8, 1-16.
11. Defant, A.; Guella, G.; Mancini, I. Synthesis and in vitro cytotoxicity evaluation of novel naphthindolizinedione derivatives. Arch. Pharm. 2007, 340, 147-153.
12. Defant, A.; Guella, G.; Mancini, I. Regioselectivity in the multi-component synthesis of indolizinoquinoline-5,12-dione derivatives. Eur. J. Org. Chem. 2006, 4201-4210.
13. Pratt, E. F.; Luckenbaugh, R. W.; Erickson, R. L. Reactions of naphthoquinones with malonic ester and its analogs, II: Reactions with acetoacetic ester and pyridine or quinoline. J. Org. Chem. 1954, 19, 176-182.
14. (a) Loupy, A.; Song, S. J.; Cho, S. J.; Park, D. K.; Kwon, T. W. Solvent-free microwave Michael addition between EMME and various nucleophiles. Synth. Commun. 2005, 35, 79-87;
15. (b) Paul, S.; Gupta, M.; Singh, P.; Gupta, R.; Loupy, A. A mild, efficient and green procedure for Michael addition of active methylene compounds to chalcones under microwave irradiation. Synth. Commun. 2005, 35, 325-332;
16. 3+-catalyzed Michael addition of 1,3-dicarbonyl compounds. Tetrahedron Lett. 1997, 38, 289-290.
17. Liu, Y.; Hu, H.-Y.; Liu, Q.-J. ; Hu, H.-W.; Xu, J.-H. Synthesis of polycyclic indolizine derivatives via one-pot tandem reactions of N-ylides with dichloro substituted α,β-unsaturated carbonyl compounds. Tetrahedron 2007, 63, 2024-2033.
18. Zhu, S.-Z.; Quin, C.-Y.; Wang, Y.-L.; Chu, Q. Preparation of 1-trifluoroacetyl indolizines and their derivatives via the cycloaddition of pyridinium N-ylides with 4-4-ethoxy 1-1,1,1-trifluorobut-3-en-one. J. Fluorine Chem. 1999, 99, 183-187.
19. Pratt, E. F.; Rice, R. G.; Luckenbaugh, R. W. Reactions of naphthoquinones with malonic ester and its analogs, III: 1-Substituted phthaloyl- and phthaloylbenzopyrrocolines. J. Am. Chem. Soc. 1957, 79, 1212-1217.
20. Kidwai, M.; Saxena, S.; Mohan, R. Microwave-induced new route to acridine and quinazoline derivatives using TLC plates. J. Heterocycl. Chem. 2005, 42, 703-705.
21. Yanni, A. S. Synthesis of some new indolizino[2,3-g]quinoline-5,12-dione derivatives. Collect. Czech. Chem. Commun. 1990, 56, 695-701.