2019
DOI: 10.1016/j.tet.2019.04.026
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Mapping the reactivity of the quinoline ring-system – Synthesis of the tetracyclic ring-system of isocryptolepine and regioisomers

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Cited by 12 publications
(38 citation statements)
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“…Applying the nitrene insertion appr to biaryls 15, 17, and 19, we were able to significantly improve the yields of tetracycl and 20 compared to our previous endeavors (Scheme 3, previous yields in brackets) Following a literature procedure, neocryptolepine (2) was obtained in good yield sta from its precursor 13 (Scheme 4) [67]. (20) using a diazotization-azidation-nitrene insertion appr ets: yields from our previous endeavors [52]. Conditions: (i) HCl (37%), NaNO2 (0 (ii) 1,2-dichlorobenzene, 180 °C, 3 h. For the synthesis of compounds 15, 17, and 1 previous work [52].…”
Section: Chemistrymentioning
confidence: 86%
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“…Applying the nitrene insertion appr to biaryls 15, 17, and 19, we were able to significantly improve the yields of tetracycl and 20 compared to our previous endeavors (Scheme 3, previous yields in brackets) Following a literature procedure, neocryptolepine (2) was obtained in good yield sta from its precursor 13 (Scheme 4) [67]. (20) using a diazotization-azidation-nitrene insertion appr ets: yields from our previous endeavors [52]. Conditions: (i) HCl (37%), NaNO2 (0 (ii) 1,2-dichlorobenzene, 180 °C, 3 h. For the synthesis of compounds 15, 17, and 1 previous work [52].…”
Section: Chemistrymentioning
confidence: 86%
“…The biological activities for the core structu sively studied while their regioisomers have bee novel pyridophenanthridine scaffold 4a (Figure represents an interesting target for biological eva eton may be regarded as a regioisomer to the pyr is illustrated in compound 5 in Figure 2), a wel notably known for exhibiting potent antiprolifer tolepine (1), nearly all naturally occurring pyrido intercalating agents, resulting in cytotoxic effect also possess the ability to inhibit topoisomerase profiles such as antibacterial, antifungal, a [53,56,57,[59][60][61]. Consequently, it is postulated thetic derivatives are pivotal for the future gener Recently, we described the preparation of s certain chemoisomers [52]. In this paper, we pre thetic strategies which allowed for the realizatio pounds 4b, 8, and 9) along with the N-alkylatio analogues (compounds 3b, 3c, 10, and 21).…”
Section: Chemistrymentioning
confidence: 99%
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