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Volumn , Issue 4, 2009, Pages 445-447

Tin triflate-mediated total synthesis of circumdatin F, sclerotigenin, asperlicin C, and other quinazolino[3,2-a][1,4]benzodiazepines

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EID: 58149477896     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b813880j     Document Type: Article
Times cited : (35)

References (27)
  • 24
    • 0003905731 scopus 로고
    • J. D. Morrison, Academic Press, New York, p. 173
    • R. R. Fraser, Asymmetric Synthesis, ed., J. D. Morrison,, Academic Press, New York, 1983, vol. 1, p. 173
    • (1983) Asymmetric Synthesis, Ed.
    • Fraser, R.R.1
  • 26
    • 29544436388 scopus 로고    scopus 로고
    • Our preliminary result indicated that, if the synthesis of 1a was carried out by conventional heating at 140°C in DMF for 3 h, 11.6% racemization was obtained (see Fig. S1 in Supplementary Information). This rapid cyclization of 4a by microwaves appeared to minimize racemization, if any. Similar experimental observations have also been reported for the Pictet-Spengler reaction:
    • N. H. Al-Said L. S. Al-Qaisi Tetrahedron Lett. 2006 47 693
    • (2006) Tetrahedron Lett. , vol.47 , pp. 693
    • Al-Said, N.H.1    Al-Qaisi, L.S.2
  • 27
    • 1842437547 scopus 로고    scopus 로고
    • 2, we investigated the screening of other metal triflates in the hope of improving the yield. We found however that, microwaving at 140°C for 30 min, in addition to unidentified side products, resulted in only low conversions (<20% in most cases) of the dehydrative cyclization reactions. Higher temperatures deteriorated the quality of reaction. Moreover, Brønsted protic acids such as triflic acid and solvents other than DMF did not improve the yields of 1b and 1f
    • J. J.-Y. Yang, Y.-H. Chu and S.-T. Chen, Optimization of Solid-Phase Combinatorial Synthesis, ed., B. Yan, and, A. W. Czarnik,, Marcel Dekker, New York, 2002, p. 305
    • (2002) Optimization of Solid-Phase Combinatorial Synthesis, Ed.
    • Yang, J.J.-Y.1    Chu, Y.-H.2    Chen, S.-T.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.