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Volumn 9, Issue 2, 2007, Pages 263-266

Stereoselective aza Diels-Alder reaction on solid phase: A facile synthesis of hexahydrocinnoline derivatives

Author keywords

[No Author keywords available]

Indexed keywords

CINNOLINE; FUSED HETEROCYCLIC RINGS; HETEROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

EID: 34047261094     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc060125l     Document Type: Article
Times cited : (38)

References (37)
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    • For introduction to heterodienophiles, see:, Trost, B. M, Fleming, I, Paquette, L. A, Eds, Pergamon Press: Oxford, U.K, Chapter 4.2, pp
    • (a) For introduction to heterodienophiles, see: Weinreb, S. M. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol 5, Chapter 4.2, pp 401-449.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 401-449
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  • 5
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    • For an overview of heterodienes, see:, Trost, B. M, Fleming, I, Paquette, L. A, Eds, Pergamon Press: Oxford, U.K, Chapter 4.3, pp
    • (b) For an overview of heterodienes, see: Boger, D. L. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol 5, Chapter 4.3, pp 451-512.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 451-512
    • Boger, D.L.1
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    • (b) Yli-Kauhaluoma, J. Tetrahedron 2001, 57, 7053-7071.
    • (2001) , vol.57 , pp. 7053-7071
    • Yli-Kauhaluoma, J.T.1
  • 10
    • 34047259203 scopus 로고
    • U.S. Patent 3222366
    • Siegfried, A. G. U.S. Patent 3222366, 1965.
    • (1965)
    • Siegfried, A.G.1
  • 16
    • 0343537654 scopus 로고    scopus 로고
    • For a review on urazoles, see
    • For a review on urazoles, see: Rádl, S. Adv. Heterocycl. Chem. 1997, 67, 119-205.
    • (1997) Adv. Heterocycl. Chem , vol.67 , pp. 119-205
    • Rádl, S.1
  • 17
    • 0001863934 scopus 로고    scopus 로고
    • Moody, C. J. Adv. Heterocycl. Chem. 1982, 30, 1-45. Our comparative [4+2] cycloaddition studies between polymer-supported diene 4 and W-phenylmaleimide (5 equiv, 24-120°C) gave clearly lower yields (10%) than using the corresponding azadienophile (PTAD) at low temperature (40%).
    • Moody, C. J. Adv. Heterocycl. Chem. 1982, 30, 1-45. Our comparative [4+2] cycloaddition studies between polymer-supported diene 4 and W-phenylmaleimide (5 equiv, 24-120°C) gave clearly lower yields (10%) than using the corresponding azadienophile (PTAD) at low temperature (40%).
  • 25
    • 34047273771 scopus 로고    scopus 로고
    • Bromo-Wang polystyrene (4-(bromomethyl)phenoxymethyl polystyrene): Novabiochem, cat. no. 01-64.-0186, 100-200 mesh, 1.6 mmol/g, cross-linked with 1% divinylbenzene (DVB).
    • Bromo-Wang polystyrene (4-(bromomethyl)phenoxymethyl polystyrene): Novabiochem, cat. no. 01-64.-0186, 100-200 mesh, 1.6 mmol/g, cross-linked with 1% divinylbenzene (DVB).
  • 27
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    • The residual bromide left on the resin 4 was determined by the volumetric Volhard method, demonstrated previously for solid support by Lu, G.-s.; Mojsov, S.; Tam, J. P.; Merrifield, R. B. J. Org. Chem. 1981, 46, 3433-3436. No residual bromide was found.
    • (b) The residual bromide left on the resin 4 was determined by the volumetric Volhard method, demonstrated previously for solid support by Lu, G.-s.; Mojsov, S.; Tam, J. P.; Merrifield, R. B. J. Org. Chem. 1981, 46, 3433-3436. No residual bromide was found.
  • 30
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    • Only traces of the minor isomer (equal m/z value) were detected on the HPLC-MS analysis (UV 210 nm) of some of the crude cycloadducts 6a-m.
    • Only traces of the minor isomer (equal m/z value) were detected on the HPLC-MS analysis (UV 210 nm) of some of the crude cycloadducts 6a-m.
  • 33
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    • Sadatake, K. JP Patent 31003121, 1956;
    • Sadatake, K. JP Patent 31003121, 1956;
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    • U.S. Patent 3267114
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    • Dubau, F. P. Chem. Ber. 1983, 116, 2714-2716.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.