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Volumn 37, Issue 28, 1996, Pages 4857-4860

A new route to 2-substituted Δ2-thiazolines: Stille cross-couplings of 2-bromo-Δ2-thiazolines

Author keywords

[No Author keywords available]

Indexed keywords

DRUG CARRIER; THIAZOLE DERIVATIVE; THIAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0030575348     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00970-7     Document Type: Article
Times cited : (22)

References (30)
  • 11
    • 0027371990 scopus 로고
    • 7. For example, in the two reported syntheses of curacin A (ref. 4c-d), 30 (two steps) and 50% yields respectively, were obtained in the cyclodehydration step leading to the thiazoline. For some recently described cyclodehydration routes to thiazolines, see: a) Vorbruggen, H.; Krolikiewicz, K. Tetrahedron 1993, 49, 9353-9372.
    • (1993) Tetrahedron , vol.49 , pp. 9353-9372
    • Vorbruggen, H.1    Krolikiewicz, K.2
  • 17
    • 85030203363 scopus 로고    scopus 로고
    • note
    • 9. All new compounds exhibited spectral data consistent with their assigned structures.
  • 18
    • 85030210917 scopus 로고    scopus 로고
    • note
    • 13C chemical shifts of the thiazolidinone carbonyl carbons (δ 174-175) and the enoltriflate carbon (δ 167-170) for a series of compounds which suggests O-triflation for triflate 2 since triflate 1 led to coupling product. These compounds and various derivatives did not provide crystals suitable for x-ray analysis.
  • 21
    • 85030199918 scopus 로고    scopus 로고
    • note
    • 20BrNOSSi (M+H) 310.0297; Found 310.0294.
  • 22
    • 85030199815 scopus 로고    scopus 로고
    • note
    • 13. Interestingly, when n-BuLi was being studied as a base for the metallation/bromination sequence, the 2-butylthiazoline i was obtained as a byproduct along with the desired bromothiazoline. (formula presented)
  • 23
    • 33645559650 scopus 로고
    • 14. Curran, D. P.; Chang, C.-T. J. Org. Chem. 1989, 54, 3140-3157. The authors thank Professor P. Wipf (Univ. of Pittsburgh) for bringing this procedure to our attention.
    • (1989) J. Org. Chem. , vol.54 , pp. 3140-3157
    • Curran, D.P.1    Chang, C.-T.2
  • 24
    • 85030209756 scopus 로고    scopus 로고
    • note
    • 15. Apparently, the vinyl adduct 11a is unstable to the reaction conditions since lower yields were obtained with longer reaction times. Purified samples of this compound stored frozen in benzene at -18°C underwent extensive decomposition in a period of several days.
  • 25
    • 85030207463 scopus 로고    scopus 로고
    • note
    • 25NOSSi : C, 62.49; H 8.19; Found: C, 62.28; H, 8.17.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.