메뉴 건너뛰기




Volumn 7, Issue 2-4, 2003, Pages 125-134

Microwave-enhanced transition metal-catalyzed decoration of 2(1H)-pyrazinone scaffolds

Author keywords

2(1H) pyrazinone; Cyanation; Dechlorination; Heck reaction; Sonogashira reaction; Stille reaction; Suzuki reaction

Indexed keywords

2(1H) PYRAZINONE; PALLADIUM; PYRAZINE DERIVATIVE; PYRAZINOIC ACID; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

EID: 0347717663     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:MODI.0000006807.43408.d5     Document Type: Article
Times cited : (59)

References (26)
  • 1
    • 84988098073 scopus 로고
    • 2(1H)-pyrazinones and 2H-1,4-oxazin-2-ones and their use in hererocyclic synthesis
    • Hoornaert, G., 2(1H)-pyrazinones and 2H-1,4-oxazin-2-ones and their use in hererocyclic synthesis, Bull. Soc. Chim. Belg., (1994)583-589.
    • (1994) Bull. Soc. Chim. Belg. , pp. 583-589
    • Hoornaert, G.1
  • 2
    • 0000687054 scopus 로고
    • Generation of specifically substituted pyridines and pyridinones from 2(1H)-pyrazinones and acetylenes: A FMO description
    • Tutonda, M., Vanderzande, D., Hendrickx, M. and Hoornaert, G., Generation of specifically substituted pyridines and pyridinones from 2(1H)-pyrazinones and acetylenes: A FMO description, Tetrahedron, 46 (1990) 5715-5732.
    • (1990) Tetrahedron , vol.46 , pp. 5715-5732
    • Tutonda, M.1    Vanderzande, D.2    Hendrickx, M.3    Hoornaert, G.4
  • 3
    • 0032558605 scopus 로고    scopus 로고
    • Synthesis of α-carbolines and β-carbolinones via intramolecular Diels-Alder reactions of 2(1H)-pyrazinones
    • Tahri, A., Buysens, K. J., Van der Eycken, E. V., Vandenberghe, D. M. and Hoornaert, G. J., Synthesis of α-carbolines and β-carbolinones via intramolecular Diels-Alder reactions of 2(1H)-pyrazinones, Tetrahedron, 54 (1998) 13211-13226.
    • (1998) Tetrahedron , vol.54 , pp. 13211-13226
    • Tahri, A.1    Buysens, K.J.2    Van Der Eycken, E.V.3    Vandenberghe, D.M.4    Hoornaert, G.J.5
  • 4
    • 0033579596 scopus 로고    scopus 로고
    • Divergent pathways in the intramolecular Diels-Alder reaction of 2(1H)-pyrazinones substituted at the 3 position with a Phenylalkyne Containing Side Chain
    • Tahri, A., De Borggraeve, W., Buysens, K., Van Meervelt, L., Compemolle, F. and Hoornaert, G. J., Divergent pathways in the intramolecular Diels-Alder reaction of 2(1H)-pyrazinones substituted at the 3 position with a Phenylalkyne Containing Side Chain, Tetrahedron, 55 (1999) 14675-14684.
    • (1999) Tetrahedron , vol.55 , pp. 14675-14684
    • Tahri, A.1    De Borggraeve, W.2    Buysens, K.3    Van Meervelt, L.4    Compemolle, F.5    Hoornaert, G.J.6
  • 5
    • 0030199652 scopus 로고    scopus 로고
    • Synthesis of new pyrrolo[3,4-b]- and [3,4-c]pyridin(on)es and related 1,7-naphthyridinones and 2,7-naphthyridines via intramolecular Diels-Alder reactions of 2(1H)-pyrazinones
    • Buysens, K. J., Vandenberghe, D. M., Hoomaert, G. J., Synthesis of new pyrrolo[3,4-b]- and [3,4-c]pyridin(on)es and related 1,7-naphthyridinones and 2,7-naphthyridines via intramolecular Diels-Alder reactions of 2(1H)-pyrazinones, Tetrahedron, 52 (1996) 9161-9178.
    • (1996) Tetrahedron , vol.52 , pp. 9161-9178
    • Buysens, K.J.1    Vandenberghe, D.M.2    Hoomaert, G.J.3
  • 6
    • 0141795494 scopus 로고    scopus 로고
    • An exploratory study on microwave-assisted solid-phase Diels-Alder reactions of 2(1H)-pyrazinones: The elaboration of a new tailor-made acid-labile linker
    • in press
    • Kaval, N., Van der Eycken, J., Caroen, J., Dehaen, W., Strohmeier, G. A., Kappe, C. O. and Van der Eycken, E., An exploratory study on microwave-assisted solid-phase Diels-Alder reactions of 2(1H)-pyrazinones: The elaboration of a new tailor-made acid-labile linker, J. Comb. Chem., 5 (2003) (in press).
    • (2003) J. Comb. Chem. , vol.5
    • Kaval, N.1    Van Der Eycken, J.2    Caroen, J.3    Dehaen, W.4    Strohmeier, G.A.5    Kappe, C.O.6    Van Der Eycken, E.7
  • 10
    • 1542420214 scopus 로고    scopus 로고
    • Generation of 6-alkylidene/benzylidene-3,6-dihydropyrazin-2(1H)-ones by reaction of 6-bromomethylpyrazin-2(1H)-ones with methoxide and further conversion into specifc piperazine-2,5-diones and pyrazin-2(1H)-ones
    • Buysens, K. J., Vandenberghe, D. M., Toppet, S. M. and Hoornaert, G. J., Generation of 6-alkylidene/benzylidene-3,6-dihydropyrazin-2(1H)-ones by reaction of 6-bromomethylpyrazin-2(1H)-ones with methoxide and further conversion into specifc piperazine-2,5-diones and pyrazin-2(1H)-ones, J. Chem. Soc. Perkin Trans. I, (1996) 231-238.
    • (1996) J. Chem. Soc. Perkin Trans. I , pp. 231-238
    • Buysens, K.J.1    Vandenberghe, D.M.2    Toppet, S.M.3    Hoornaert, G.J.4
  • 11
    • 0036828174 scopus 로고    scopus 로고
    • High-speed microwave promoted hetero-Diels-Alder reactions of 2(1H)-pyrazinones in ionic liquid doped solvents
    • Van der Eycken, E., Appukkuttan, P., De Borggraeve, W., Dehaen, W., Dallinger, D. and Kappe, C. O., High-speed microwave promoted hetero-Diels-Alder reactions of 2(1H)-pyrazinones in ionic liquid doped solvents, J. Org. Chem, 67 (2002) 7904-7907.
    • (2002) J. Org. Chem. , vol.67 , pp. 7904-7907
    • Van Der Eycken, E.1    Appukkuttan, P.2    De Borggraeve, W.3    Dehaen, W.4    Dallinger, D.5    Kappe, C.O.6
  • 12
    • 0345834954 scopus 로고    scopus 로고
    • Wiley-VCH Weinheim, Chapter 11 by Olofsson, K., Hallberg, A. and Larhed, M.
    • For an overview see Loupy, A., Microwaves in Organic Synthesis, Wiley-VCH Weinheim, 2002, Chapter 11 by Olofsson, K., Hallberg, A. and Larhed, M., pp. 379-403.
    • (2002) Microwaves in Organic Synthesis , pp. 379-403
    • Loupy, A.1
  • 13
    • 0036738330 scopus 로고    scopus 로고
    • Microwave-accelerated homogeneous catalysis in organic chemistry
    • Larhed, M., Moberg, Ch. and Hallberg., A. Microwave-accelerated homogeneous catalysis in organic chemistry, Acc. Chem. Res., 35 (2002) 717-727.
    • (2002) Acc. Chem. Res. , vol.35 , pp. 717-727
    • Larhed, M.1    Moberg, Ch.2    Hallberg, A.3
  • 15
    • 0345005012 scopus 로고    scopus 로고
    • Microwave-assisted aqueous Suzuki cross-coupling reactions
    • Blettner, C. G., König, W. A., Stenzel, W. and Schotten, T., Microwave-assisted aqueous Suzuki cross-coupling reactions, J. Org. Chem., 64 (1999) 3885-3890.
    • (1999) J. Org. Chem. , vol.64 , pp. 3885-3890
    • Blettner, C.G.1    König, W.A.2    Stenzel, W.3    Schotten, T.4
  • 16
    • 0033638806 scopus 로고    scopus 로고
    • Microwave-promoted palladium catalyzed Heck cross coupling reaction in Water
    • Wang, J. X., Hu, Z., Wei, B. G. and Bai, L., Microwave-promoted palladium catalyzed Heck cross coupling reaction in Water, J. Chem. Res., Synop., (2000) 484-485.
    • (2000) J. Chem. Res., Synop. , pp. 484-485
    • Wang, J.X.1    Hu, Z.2    Wei, B.G.3    Bai, L.4
  • 17
    • 0005854516 scopus 로고    scopus 로고
    • Carbon-carbon bond formation via palladium-catalyzed reductive coupling of aryl halides in air and water
    • Venkatraman, S., Huang, T. and Li, C.-J., Carbon-carbon bond formation via palladium-catalyzed reductive coupling of aryl halides in air and water, Adv. Synth. Catal., 344 (2002) 399-405.
    • (2002) Adv. Synth. Catal. , vol.344 , pp. 399-405
    • Venkatraman, S.1    Huang, T.2    Li, C.-J.3
  • 18
    • 0028944048 scopus 로고
    • Palladium-catalyzed Stille couplings of aryl-, vinyl- and alkyltrichlorostannanes in aqueous solution
    • (a) Rai, R., Aubrecht, K. B. and Collum, D. B., Palladium-catalyzed Stille couplings of aryl-, vinyl- and alkyltrichlorostannanes in aqueous solution, Tetrahedron Lett., 36 (1995) 3111-3114.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 3111-3114
    • Rai, R.1    Aubrecht, K.B.2    Collum, D.B.3
  • 19
    • 0028894576 scopus 로고
    • Palladium-catalyzed cross-coupling reaction of organostannoates with aryl halides in aqueous medium
    • (b) Roshchin, A. I., Bumagin, N. A. and Beletskaya, I. P., Palladium-catalyzed cross-coupling reaction of organostannoates with aryl halides in aqueous medium, Tetrahedron Lett., 36 (1995) 125-128.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 125-128
    • Roshchin, A.I.1    Bumagin, N.A.2    Beletskaya, I.P.3
  • 20
    • 0037989563 scopus 로고    scopus 로고
    • Recent developments of palladium (0) catalyzed reactions in aqueous media
    • (c) Genet, J. P. and Savignac, M., Recent developments of palladium (0) catalyzed reactions in aqueous media. J. Organomet. Chem., 576 (1999) 305-317.
    • (1999) J. Organomet. Chem. , vol.576 , pp. 305-317
    • Genet, J.P.1    Savignac, M.2
  • 21
    • 0035601437 scopus 로고    scopus 로고
    • Polyethylene glycol as support and phase transfer catalyst in aqueous palladium-catalyzed liquid-phase synthesis
    • Xia, M. and Wang, Y. G., Polyethylene glycol as support and phase transfer catalyst in aqueous palladium-catalyzed liquid-phase synthesis, Chinese Chem. Lett., 12 (2001) 941-942.
    • (2001) Chinese Chem. Lett. , vol.12 , pp. 941-942
    • Xia, M.1    Wang, Y.G.2
  • 22
    • 0000153468 scopus 로고    scopus 로고
    • Microwave-promoted palladium-catalyzed coupling reactions
    • Larhed, M. and Hallberg, A., Microwave-promoted palladium-catalyzed coupling reactions, J. Org. Chem., 61 (1996) 9582-9584.
    • (1996) J. Org. Chem. , vol.61 , pp. 9582-9584
    • Larhed, M.1    Hallberg, A.2
  • 23
    • 0034680614 scopus 로고    scopus 로고
    • Fast microwave-assisted preparation of aryl and vinyl nitriles and the corresponding tetrazoles from organo-halides
    • and references cited
    • Alterman, M. and Hallberg, A., Fast microwave-assisted preparation of aryl and vinyl nitriles and the corresponding tetrazoles from organo-halides, J. Org. Chem., 65 (2000) 7984-7989 and references cited.
    • (2000) J. Org. Chem. , vol.65 , pp. 7984-7989
    • Alterman, M.1    Hallberg, A.2
  • 24
    • 0035874744 scopus 로고    scopus 로고
    • Rapid homogeneous-phase Sonogashira coupling reactions using controlled microwave heating
    • Erdélyi, M. and Gogoll, A., Rapid homogeneous-phase Sonogashira coupling reactions using controlled microwave heating, J. Org. Chem., 66 (2001) 4165-4169.
    • (2001) J. Org. Chem. , vol.66 , pp. 4165-4169
    • Erdélyi, M.1    Gogoll, A.2
  • 25
    • 0037238556 scopus 로고    scopus 로고
    • An alkyne metathesis-based route to ortho-dehydrobenzannulenes
    • Miljanic, O. S., Vollhardt, K. P. C. and Whitener, G. D. An alkyne metathesis-based route to ortho-dehydrobenzannulenes, Synlett, (2003) 29-34.
    • (2003) Synlett , pp. 29-34
    • Miljanic, O.S.1    Vollhardt, K.P.C.2    Whitener, G.D.3
  • 26
    • 0035888212 scopus 로고    scopus 로고
    • Intramolecular Diels-Alder reactions of N-alkenyl-2(1H)-pyrazinones: Generation of a novel type of cis-1,7-naphthyridine
    • Rombouts, J. R., De Borggraeve, W., Toppet, S. M., Compernolle, F. and Hoornaert, G. J., Intramolecular Diels-Alder reactions of N-alkenyl-2(1H)-pyrazinones: Generation of a novel type of cis-1,7-naphthyridine, Tetrahedron Lett., 42 (2001) 7397-7399.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 7397-7399
    • Rombouts, J.R.1    De Borggraeve, W.2    Toppet, S.M.3    Compernolle, F.4    Hoornaert, G.J.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.