메뉴 건너뛰기




Volumn 40, Issue 3, 2010, Pages 361-369

Synthesis of electron-deficient 1,3,5-triazines as potential azadienes for inverse-electron-demand Diels-Alder reactions

Author keywords

1,3,5 triazines; Inverse electron demand Diels Alder reaction; LUMO energies; Solubility

Indexed keywords

ACYL DERIVATIVE; ALCOHOL DERIVATIVE; ALKADIENE; AMIDE; AMINE; AZADIENE DERIVATIVE; CHLORIDE; ESTER; ETHANETHIOL; THIOESTER; THIOL; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 73949159498     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910902978031     Document Type: Article
Times cited : (5)

References (21)
  • 3
    • 0029844731 scopus 로고    scopus 로고
    • Azadiene Diels-Alder reactions: Scope and applications: Total synthesis of natural and ent-fredericamycin A.
    • Boger, D. L. Azadiene Diels-Alder reactions: Scope and applications: Total synthesis of natural and ent-fredericamycin A. J. Heterocycl. Chem. 1996, 33, 1519-1531.
    • (1996) J. Heterocycl. Chem. , vol.33 , pp. 1519-1531
    • Boger, D.L.1
  • 4
    • 84988099599 scopus 로고
    • Novel cycloaddition routes to fused heterocycles
    • Taylor, E. C. Novel cycloaddition routes to fused heterocycles. Bull. Soc. Chim. Belg. 1988, 97, 599-613.
    • (1988) Bull. Soc. Chim. Belg. , vol.97 , pp. 599-613
    • Taylor, E.C.1
  • 5
    • 3643133641 scopus 로고
    • Cycloadditionen mit Azabenzolen, X: Cycloadditionen mit 1,3,5-triazinen.
    • Neunhoeffer, H.; Bachmann, M. Cycloadditionen mit Azabenzolen, X: Cycloadditionen mit 1,3,5-triazinen. Chem. Ber. 1975, 108, 3877-3882.
    • (1975) Chem. Ber. , Issue.108 , pp. 3877-3882
    • Neunhoeffer, H.1    Bachmann, M.2
  • 6
    • 0001198391 scopus 로고
    • Inverse electron demand Diels-Alder reactions of heterocyclic azadienes: [4 + 2] Cycloaddition reaction of amidines with 1,3,5-triazines.
    • Boger, D. L.; Kochanny, M. J. Inverse electron demand Diels-Alder reactions of heterocyclic azadienes: [4 + 2] Cycloaddition reaction of amidines with 1,3,5-triazines. J. Org. Chem. 1994, 59, 4950-4955.
    • (1994) J. Org. Chem. , vol.59 , pp. 4950-4955
    • Boger, D.L.1    Kochanny, M.J.2
  • 7
    • 0000450357 scopus 로고
    • Inverse electron demand Diels-Alder reactions of 2,4,6-(ethoxycarbonyl)- l,3,5-triazine and 2,4,6-(methylthio)-1,3,5-triazine: Pyrimidine introduction.
    • Boger, D. L.; Dang, Q. Inverse electron demand Diels-Alder reactions of 2,4,6-(ethoxycarbonyl)-l,3,5-triazine and 2,4,6-(methylthio)-1,3,5-triazine: Pyrimidine introduction. Tetrahedron 1988, 44, 3379-3390.
    • (1988) Tetrahedron , vol.44 , pp. 3379-3390
    • Boger, D.L.1    Dang, Q.2
  • 8
    • 0001153084 scopus 로고
    • Thermal cycloaddition of 1,3,5-triazine with enamines: Regiospecific pyrimidine annulation.
    • Boger, D. L.; Schumacher, J.; Mullican, M. D.; Patel, M.; Panek, J. S. Thermal cycloaddition of 1,3,5-triazine with enamines: Regiospecific pyrimidine annulation. J. Org. Chem. 1982, 47, 2673-2675.
    • (1982) J. Org. Chem. , vol.47 , pp. 2673-2675
    • Boger, D.L.1    Schumacher, J.2    Mullican, M.D.3    Patel, M.4    Panek, J.S.5
  • 9
    • 0029744577 scopus 로고    scopus 로고
    • 5-Aminopyrazoles as dienophiles in the inverse electron demand Diels-Alder reactions of 2,4,6-tris(ethoxycarbonyl)-1,3,5-triazine: Syntheses of pyrazolopyrimidines.
    • Dang, Q.; Brown, B. S.; Erion, M. D. 5-Aminopyrazoles as dienophiles in the inverse electron demand Diels-Alder reactions of 2,4,6-tris(ethoxycarbonyl)- 1,3,5-triazine: Syntheses of pyrazolopyrimidines. J. Org. Chem. 1996, 61, 5204-5205.
    • (1996) J. Org. Chem. , vol.61 , pp. 5204-5205
    • Dang, Q.1    Brown, B.S.2    Erion, M.D.3
  • 10
    • 0033597618 scopus 로고    scopus 로고
    • Efficient synthesis of purines and purine nucleosides via an inverse electron demand Diels-Alder reaction.
    • Dang, Q.; Liu, Y.; Erion, M. D. Efficient synthesis of purines and purine nucleosides via an inverse electron demand Diels-Alder reaction. J. Am. Chem. Soc. 1999, 121, 5833-5834.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 5833-5834
    • Dang, Q.1    Liu, Y.2    Erion, M.D.3
  • 11
    • 0037195753 scopus 로고    scopus 로고
    • An efficient synthesis of pyrrolo[2,3-d]pyrimidines via inverse electron demand Diels-Alder reactions of 2-amino-4-cyanopyrroles with 1,3,5-triazines.
    • Dang, Q.; Gomez-Galeno, J. E. An efficient synthesis of pyrrolo[2,3-d]pyrimidines via inverse electron demand Diels-Alder reactions of 2-amino-4-cyanopyrroles with 1,3,5-triazines. J. Org. Chem. 2002, 67, 8703-8705.
    • (2002) J. Org. Chem. , vol.67 , pp. 8703-8705
    • Dang, Q.1    Gomez-Galeno, J.E.2
  • 13
    • 0028095613 scopus 로고
    • Total synthesis of bleomycin A2 and related agents 2: Synthesis of (-)-pyrimidoblamic acid, epi-(+)-pyrimidoblamic acid, (+)- desacetamidopyrimidoblamic acid, and (-)-descarboxamidopyrimidoblamic acid.
    • Boger, D. L.; Honda, T.; Dang, Q. Total synthesis of bleomycin A2 and related agents, 2: Synthesis of (-)-pyrimidoblamic acid, epi-(+)-pyrimidoblamic acid, (+)-desacetamidopyrimidoblamic acid, and (-)-descarboxamidopyrimidoblamic acid. J. Am. Chem. Soc. 1994, 116, 5619-5630.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 5619-5630
    • Boger, D.L.1    Honda, T.2    Dang, Q.3
  • 14
    • 0346650051 scopus 로고    scopus 로고
    • Catalytic cyclotrimerization of arylnitriles using the novel samarium(ii) complexes as catalysts.
    • Xu, F.; Zhu, X.; Shen, Q.; Lu, J.; Li, J. Catalytic cyclotrimerization of arylnitriles using the novel samarium(ii) complexes as catalysts. Chin. J. Chem. 2002, 20, 1334-1339.
    • (2002) Chin. J. Chem. , vol.20 , pp. 1334-1339
    • Xu, F.1    Zhu, X.2    Shen, Q.3    Lu, J.4    Li, J.5
  • 16
    • 0001096422 scopus 로고    scopus 로고
    • Synthesis of differentially substituted hexaethynylbenzenes based on tandem Sonogashira and Negishi cross-coupling reactions.
    • Sonoda, M.; Inaba, A.; Itahashi, K.; Tobe, Y. Synthesis of differentially substituted hexaethynylbenzenes based on tandem Sonogashira and Negishi cross-coupling reactions. Org. Lett. 2001, 3, 2419-2421.
    • (2001) Org. Lett. , vol.3 , pp. 2419-2421
    • Sonoda, M.1    Inaba, A.2    Itahashi, K.3    Tobe, Y.4
  • 17
    • 0343471420 scopus 로고    scopus 로고
    • First 2,3-dialkynyl-1,4-diazabutadienes by Pd-catalyzed cross-coupling of bis(imidoyl chlorides) and alkynylstannanes
    • Faust, R.; Gobelt, B. First 2,3-dialkynyl-1,4-diazabutadienes by Pd-catalyzed cross-coupling of bis(imidoyl chlorides) and alkynylstannanes. Tetrahedron Lett. 1997, 38, 8017-8020.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 8017-8020
    • Faust, R.1    Gobelt, B.2
  • 18
    • 0001595852 scopus 로고
    • Transesterification
    • Otera, J. Transesterification. Chem. Rev. 1993, 93, 1449-1470.
    • (1993) Chem. Rev. , vol.93 , pp. 1449-1470
    • Otera, J.1
  • 19
    • 33947467815 scopus 로고
    • XVII: S-Triazine from s-triazine-2,4,6-tricarbonic acid.
    • Grundmann, C; Kober, E. Triazines, XVII: s-Triazine from s-triazine-2,4,6-tricarbonic acid. J. Org. Chem. 1956, 21, 1392-1394.
    • (1956) J. Org. Chem. , vol.21 , pp. 1392-1394
    • Grundmann, C.1    Triazines, K.E.2
  • 21
    • 0035955807 scopus 로고    scopus 로고
    • A tandem decarboxylation=Diels-Alder reaction of 5-amino-1-phenyl-4- pyrazolecarboxylic acid with 1,3,5-triazines.
    • Dang, Q.; Liu, Y.; Sun, Z. A tandem decarboxylation=Diels-Alder reaction of 5-amino-1-phenyl-4-pyrazolecarboxylic acid with 1,3,5-triazines. Tetrahedron Lett. 2001, 42, 8419-8422.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 8419-8422
    • Dang, Q.1    Liu, Y.2    Sun, Z.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.