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Volumn 5, Issue 18, 2003, Pages 3333-3335

Cytosine analogues from substituted acetonitriles via Thorpe condensation

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE DERIVATIVE; CYTOSINE DERIVATIVE;

EID: 0141856192     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035223j     Document Type: Article
Times cited : (16)

References (20)
  • 3
    • 0027449157 scopus 로고
    • 2CN, reflux): (a) Benarab, A.; Boyé, S.; Savelon, L.; Guillaumet, G. Tetrahedron Lett. 1993, 34, 7567-7568. (b) Rooney, C. S.; Stuart, R. S.; Wasson, B. K.; Williams, H. W. R. Can. J. Chem. 1975, 53, 2279-2292.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 7567-7568
    • Benarab, A.1    Boyé, S.2    Savelon, L.3    Guillaumet, G.4
  • 8
    • 0141692436 scopus 로고
    • Cross coupling between the anion of an alkyl nitrile and a α-branched cyanomethyl ether at low temperature has been reported: Kobayashi, K.; Hiyama, T. Tetrahedron Lett. 1983, 24, 3509-3512.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 3509-3512
    • Kobayashi, K.1    Hiyama, T.2
  • 10
  • 11
    • 0033591117 scopus 로고    scopus 로고
    • For additions of alkylmetals to cyanomethyl ethers, see: (a) Charette, A. B.; Gagnon, A. Tetrahedron: Asymmetry 1999, 10, 1961-1968. (b) Charette, A. B. ; Gagnon, A.; Janes, M.; Mellon, C. Tetrahedron Lett. 1998, 39, 5147-5150. (c) Kuwahara, Y.; Yen, L. T. M.; Tominaga, Y.; Matsumoto, K.; Wada, Y. Agric. Biol. Chem. 1982, 46, 2283-2291.
    • (1999) Tetrahedron: Asymmetry , vol.10 , pp. 1961-1968
    • Charette, A.B.1    Gagnon, A.2
  • 12
    • 0032537710 scopus 로고    scopus 로고
    • For additions of alkylmetals to cyanomethyl ethers, see: (a) Charette, A. B.; Gagnon, A. Tetrahedron: Asymmetry 1999, 10, 1961-1968. (b) Charette, A. B. ; Gagnon, A.; Janes, M.; Mellon, C. Tetrahedron Lett. 1998, 39, 5147-5150. (c) Kuwahara, Y.; Yen, L. T. M.; Tominaga, Y.; Matsumoto, K.; Wada, Y. Agric. Biol. Chem. 1982, 46, 2283-2291.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 5147-5150
    • Charette, A.B.1    Gagnon, A.2    Janes, M.3    Mellon, C.4
  • 13
    • 0020367708 scopus 로고
    • For additions of alkylmetals to cyanomethyl ethers, see: (a) Charette, A. B.; Gagnon, A. Tetrahedron: Asymmetry 1999, 10, 1961-1968. (b) Charette, A. B. ; Gagnon, A.; Janes, M.; Mellon, C. Tetrahedron Lett. 1998, 39, 5147-5150. (c) Kuwahara, Y.; Yen, L. T. M.; Tominaga, Y.; Matsumoto, K.; Wada, Y. Agric. Biol. Chem. 1982, 46, 2283-2291.
    • (1982) Agric. Biol. Chem. , vol.46 , pp. 2283-2291
    • Kuwahara, Y.1    Yen, L.T.M.2    Tominaga, Y.3    Matsumoto, K.4    Wada, Y.5
  • 14
    • 0141469229 scopus 로고    scopus 로고
    • note
    • Crystallographic data for this compound has been deposited with the Cambridge Crystallographic Data Centre. The coordinates can be obtained on request from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.
  • 15
    • 0141580876 scopus 로고    scopus 로고
    • note
    • 3C(O)NCO, TMSNCO, and TsNCO).
  • 16
    • 0141804019 scopus 로고    scopus 로고
    • note
    • Isomer ratios of ureas 3 were unchanged from the corresponding enaminonitrile starting material.
  • 17
    • 0141469228 scopus 로고    scopus 로고
    • note
    • Enamines 3 must undergo Z/E isomerization to cyclize. This isomerization presumably occurs through a base-catalyzed enamine-imine tautomerization.
  • 18
    • 0036135888 scopus 로고    scopus 로고
    • For a review of the intramolecular Thorpe-Ziegler cyclization, see: Fleming, F. F.; Shook, B. C. Tetrahedron 2002, 58, 1-23.
    • (2002) Tetrahedron , vol.58 , pp. 1-23
    • Fleming, F.F.1    Shook, B.C.2
  • 19
    • 0141580875 scopus 로고    scopus 로고
    • note
    • It was found that dimer 10 codistills with many common organic solvents, including diethyl ether, hexanes, and ethyl acetate. Better yields of the corresponding urea were obtained when 10 was acylated directly without purification.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.