메뉴 건너뛰기




Volumn 63, Issue 12, 2007, Pages 2695-2711

Synthesis of 3-substituted indazoles and benzoisoxazoles via Pd-catalyzed cyclization reactions: application to the synthesis of nigellicine

Author keywords

Amination; Benzoisoxazole; Hydrazone; Indazole; Nigellicine; Palladium

Indexed keywords

1 (2 BROMOPHENYL) 2 METHYLPROPAN 1 ONE 4 METHYLPHENYLSULFONYLHYDRAZONE; 2 (NONAFLUOROBUTANESULFONYLOXY)BENZOPHENONE 4 METHYLPHENYLSULFONYLHYDRAZONE; 2 (NONAFLUOROBUTANESULFONYLOXY)BENZOPHENONE OXIME; 2 BROMO 4 METHYLBENZOPHENONE 4 METHYLPHENYLSULFONYLHYDRAZONE; 2 BROMO 4 NITROBENZOPHENONE 4 METHYLPHENYLSULFONYLHYDRAZONE; 2 BROMO 4 NITROBENZOPHENONE OXIME; 2 BROMO 4' METHOXYBENZOPHENONE 4 METHYLPHENYLSULFONYLHYDRAZONE; 2 BROMO 5 METHOXYBENZOPHENONE 4 METHYLPHENYLSULFONYLHYDRAZONE; 2 BROMO 5 METHOXYBENZOPHENONE OXIME; 2 BROMOBENZOPHENONE 4 METHYLPHENYLSULFONYLHYDRAZONE; 2 BROMOBENZOPHENONE OXIME; 2 CHLOROBENZOPHENONE OXIME; 2 CHLOROPROPIOPHENONE 4 METHYLPHENYLSULFONYLHYDRAZONE; 3 (2 BROMOPYRIDINYL) PHENYLKETONE 4 METHYLPHENYLSULFONYLHYDRAZONE; ALKALOID DERIVATIVE; BROMOACETOPHENONE 4 METHYLPHENYLSULFONYLHYDRAZONE; CARBON; HYDRAZONE DERIVATIVE; INDAZOLE DERIVATIVE; ISOXAZOLE DERIVATIVE; N,N DIETHYL 2 (2 BROMOPHENYL) 2 OXOACETAMIDE 4 METHYLPHENYLSULFONYLHYDRAZONE; NIGEGLANINE; NIGELLICINE; NIGELLIDINE; NITROGEN; OXIME DERIVATIVE; OXYGEN; PALLADIUM; TERT BUTYL 2 (2 BROMOPHENYL) 2 OXOACETATE 4 METHYLPHENYLSULFONYLHYDRAZONE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

EID: 33846930164     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.01.010     Document Type: Article
Times cited : (98)

References (59)
  • 11
    • 33846932709 scopus 로고    scopus 로고
    • For the construction of indazole ring system by N1-N2 bond formation, see:
  • 17
    • 33846931483 scopus 로고    scopus 로고
    • For the construction of indazole ring system by N2-C3 bond formation, see:
  • 20
    • 33846913616 scopus 로고    scopus 로고
    • For the construction of indazole ring system by N1-C7a bond formation, see:
  • 25
    • 0029044538 scopus 로고
    • For reviews on Pd-catalyzed amination reaction, see:
    • Louie J., and Hartwig J.F. Tetrahedron Lett. 36 (1995) 3609-3612 For reviews on Pd-catalyzed amination reaction, see:
    • (1995) Tetrahedron Lett. , vol.36 , pp. 3609-3612
    • Louie, J.1    Hartwig, J.F.2
  • 28
    • 0008165462 scopus 로고    scopus 로고
    • For intermolecular Pd-catalyzed amination reaction of hydrazones, see:
    • Yang B.H., and Buchwald S.L. J. Organomet. Chem. 576 (1999) 125-146 For intermolecular Pd-catalyzed amination reaction of hydrazones, see:
    • (1999) J. Organomet. Chem. , vol.576 , pp. 125-146
    • Yang, B.H.1    Buchwald, S.L.2
  • 30
    • 0037128497 scopus 로고    scopus 로고
    • For intramolecular Pd-catalyzed amination reaction of hydrazones, see:
    • Haddad N., and Baron J. Tetrahedron Lett. 43 (2002) 2171-2173 For intramolecular Pd-catalyzed amination reaction of hydrazones, see:
    • (2002) Tetrahedron Lett. , vol.43 , pp. 2171-2173
    • Haddad, N.1    Baron, J.2
  • 35
    • 33846937751 scopus 로고    scopus 로고
    • For functionalization of 3-position of indazoles, see:
  • 40
    • 33846939945 scopus 로고    scopus 로고
    • note
    • It should also be noted that mild intramolecular Pd-catalyzed amination reaction is still much rarer than that of intermolecular version in the literature.
  • 46
    • 0037120256 scopus 로고    scopus 로고
    • For E/Z isomerization of ortho-palladated acetophenonephenylhydrazone, see:
    • For E/Z isomerization of ortho-palladated acetophenonephenylhydrazone, see:. Carbayo A., Cuevas J.V., and García-Herbosa G. J. Organomet. Chem. 658 (2002) 15-20
    • (2002) J. Organomet. Chem. , vol.658 , pp. 15-20
    • Carbayo, A.1    Cuevas, J.V.2    García-Herbosa, G.3
  • 47
    • 33846907085 scopus 로고
    • Decomposition pathway of hydrazones is also not yet clear, however, carbene formation might be occurring during the reaction, see:
    • Decomposition pathway of hydrazones is also not yet clear, however, carbene formation might be occurring during the reaction, see:. Dellacoletta B.A., and Shechter H. Tetrahedron Lett. 20 (1979) 4817-4820
    • (1979) Tetrahedron Lett. , vol.20 , pp. 4817-4820
    • Dellacoletta, B.A.1    Shechter, H.2
  • 49
    • 33846900138 scopus 로고    scopus 로고
    • Benzoisoxazoles also form the nucleus of biologically active compounds. For selected recent examples, see:
  • 53
    • 20544475280 scopus 로고    scopus 로고
    • Very recently, Kelly reported the first total synthesis of nigellicine and nigeglanine, see:
    • Very recently, Kelly reported the first total synthesis of nigellicine and nigeglanine, see:. Elliott E.L., Bushell S.M., Cavero M., Tolan B., and Kelly T.R. Org. Lett. 7 (2005) 2449-2451
    • (2005) Org. Lett. , vol.7 , pp. 2449-2451
    • Elliott, E.L.1    Bushell, S.M.2    Cavero, M.3    Tolan, B.4    Kelly, T.R.5
  • 55
    • 0037467813 scopus 로고    scopus 로고
    • α-Ketoester 14 was best generated by the modified method of Ruchirawat's procedure, see:
    • α-Ketoester 14 was best generated by the modified method of Ruchirawat's procedure, see:. Thasana N., Prachyawarakorn V., Tontoolarug S., and Ruchirawat S. Tetrahedron Lett. 44 (2003) 1019-1021
    • (2003) Tetrahedron Lett. , vol.44 , pp. 1019-1021
    • Thasana, N.1    Prachyawarakorn, V.2    Tontoolarug, S.3    Ruchirawat, S.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.