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Volumn , Issue 15, 2008, Pages 2339-2341

Iminophosphorane-mediated synthesis of cyclic guanidines: Application to the synthesis of a simplified NA22598A1 analogue

Author keywords

Antitumor agents; Azides; Cyclizations; Heterocycles; Stereoselective synthesis

Indexed keywords

2 IMINOIMIDAZOLIDINE DERIVATIVE; ALKANE DERIVATIVE; ANTINEOPLASTIC AGENT; AZIDE; BETA AMINO AZIDE; BIS(DIPHENYLPHOSPHINO)BUTANE; GUANIDINE DERIVATIVE; IMIDAZOLIDINE DERIVATIVE; IMINOPHOSPHORANE; ISOCYANIC ACID DERIVATIVE; NA 22598A1; PHOSPHORANE DERIVATIVE; TOSYL ISOCYANATE; UNCLASSIFIED DRUG;

EID: 52949147802     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078279     Document Type: Article
Times cited : (5)

References (23)
  • 4
    • 33846111293 scopus 로고    scopus 로고
    • 1, see: Tsuchiya, S.; Sunazuka, T.; Hirose, T.; Mori, R.; Tanaka, T.; Iwatsuki, M.; Omura, S. Org. Lett. 2006, 8, 5577; and references therein.
    • 1, see: Tsuchiya, S.; Sunazuka, T.; Hirose, T.; Mori, R.; Tanaka, T.; Iwatsuki, M.; Omura, S. Org. Lett. 2006, 8, 5577; and references therein.
  • 16
    • 0032532253 scopus 로고    scopus 로고
    • Bis(diphenylphosphino)ethane has been used to address similar problems in Staudinger and Mitsunobu reactions, see: O'Neil, I. A.; Thompson, S.; Murray, C. L.; Kalindjian, S. B. Tetrahedron Lett. 1998, 39, 7787.
    • Bis(diphenylphosphino)ethane has been used to address similar problems in Staudinger and Mitsunobu reactions, see: O'Neil, I. A.; Thompson, S.; Murray, C. L.; Kalindjian, S. B. Tetrahedron Lett. 1998, 39, 7787.
  • 17
    • 52949097164 scopus 로고    scopus 로고
    • 2) gave 7 (0.24 g, 71%) as a white solid.
    • 2) gave 7 (0.24 g, 71%) as a white solid.
  • 18
    • 52949094192 scopus 로고    scopus 로고
    • Selected Spectroscopic Data: 7: mp 152-153°C (from CH 2Cl2-Et2O, 1H NMR (400 MHz, CDCl3, δ, 7.81 (d, J, 8.3 Hz, 2 H, ArH, 7.71 (s, 1 H, NH, 7.29-7.37 (m, 5 H, ArH, 7.22 (d, J, 8.3 Hz, 2 H, ArH, 5.25 (s, 2 H, OCH2Ph, 3.90-3.95 (m, 2 H, 3.60-3.65 (m, 2 H, 2.40 (s, 3 H, Me, 13C NMR (100.5 MHz, CDCl3, δ, 154.1 (C, 150.8 (C, 142.6 (C, 139.7 (C, 135.1 (C, 129.3 (CH, 128.6 (CH, 128.3 (CH, 128.0 (CH, 126.3 (CH, 68.5 (CH2, 43.9 (CH2, 39.9 (CH2, 21.5 (Me, IR (neat, 3315, 2919, 1753, 1621 cm-1. MS (FAB, m/z, 374 [M, H, 330. HRMS (FAB , m/z [M, H, calcd for C18H 20N3O4S: 374.1175; found: 374.1179. 16: [α]D24 47 c, 1.2, EtOH, 1H NM
    • 8S: 776.3693; found: 776.3692.
  • 19
    • 52949142151 scopus 로고    scopus 로고
    • This data has been deposited at the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK. Deposition number: CCDC 679310
    • This data has been deposited at the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK. Deposition number: CCDC 679310.
  • 20
    • 52949097557 scopus 로고    scopus 로고
    • R [(R)-9] = 14.8 min.
    • R [(R)-9] = 14.8 min.
  • 21
    • 0031849499 scopus 로고    scopus 로고
    • and references cited therein. For example, see
    • For example, see: Hodgkinson, T. J.; Shipman, M. Synthesis 1998, 1141; and references cited therein.
    • (1998) Synthesis , pp. 1141
    • Hodgkinson, T.J.1    Shipman, M.2
  • 22
    • 52949091082 scopus 로고    scopus 로고
    • 2, 16 h, 90%).
    • 2, 16 h, 90%).
  • 23
    • 52949124349 scopus 로고    scopus 로고
    • This contamination arises from the fact that solid NH4Cl is used to quench the dissolving metal reduction and TFA is used as a co-solvent in the subsequent purification by silica gel chromatography. The effective molarity of 17 in D2O, from which the yield could be estimated, was determined by adding known quantities of 1,4-dioxane to the sample and subsequent quantification of the dioxane/17 ratio by 1H NMR integration
    • 1H NMR integration.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.