123719-47-1Relevant academic research and scientific papers
Transition metal complexes in organic synthesis, Part 53. Iron-mediated synthesis of hyellazole and isohyellazole
Knoelker, Hans-Joachim,Baum, Elke,Hopfmann, Thomas
, p. 10391 - 10412 (1999)
The synthesis of the marine alkaloid hyellazole and the non-natural regioisomer isohyellazole is reported starting from the tricarbonyliron- complexed cyclohexadienylium cation and the fully functionalized arylamines by electrophilic aromatic substitution
Diversity oriented convergent access for collective total synthesis of bioactive multifunctional carbazole alkaloids: Synthesis of carbazomycin A, carbazomycin B, hyellazole, chlorohyellazole, and clausenaline D
Markad, Shivaji B.,Argade, Narshinha P.
, p. 5470 - 5473 (2014)
Facile syntheses of imperative carbazole alkaloids carbazomycin A, carbazomycin B, hyellazole, chlorohyellazole, and clausenaline D have been demonstrated starting from readily available Boc-protected 3-formylindole and dimethyl maleate. The suitably subs
Transition Metal-Diene Complexes in Organic Synthesis, Part 23. Total Synthesis of the Marine Alkaloid Hyellazole
Knoelker, Hans-Joachim,Baum, Elke,Hopfmann, Thomas
, p. 5339 - 5342 (1995)
The marine alkaloid hyellazole has been synthesized in a convergent manner from the tricarbonyliron-complexed cyclohexadienylium cation and a fully functionalized arylamine by an electrophilic aromatic substitution and subsequent oxidative cyclization.
Construction of highly functionalized carbazoles via condensation of an enolate to a nitro group
Poudel, Tej Narayan,Lee, Yong Rok
, p. 7028 - 7033 (2015)
This paper describes a novel synthesis of highly functionalized and diverse carbazoles via transition-metal-free and mild base-promoted condensations of readily available 2-nitrocinnamaldehyde or 2-nitrochalcones with various β-ketoesters or 1,3-diaryl-2-
A short divergent approach to highly substituted carbazoles and β-carbolines via in situ-generated diketoindoles
Untergehrer, Martin,Bracher, Franz
supporting information, (2020/03/03)
Based on an aza-alkylation/Michael addition cascade reaction developed by Kim and co-workers we have developed divergent cascade reactions leading to either highly substituted 1-hydroxycarbazoles, 3-hydroxycarbazoles or β-carbolines, starting from readily
New Carbazoles and Preparation method thereof
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Paragraph 0060; 0145-0146, (2017/05/05)
The present invention relates to a novel carbazole derivative, and to a production method thereof. More specifically, the production method involves the use of a starting material which can be industrially obtainable without using transition metal, and th
Synthesis of substituted carbazoles and β-carbolines by cyclization of diketoindole derivatives
Duval, Eric,Cuny, Gregory D.
, p. 5411 - 5413 (2007/10/03)
A new route to substituted β-carbolines and carbazoles is described. Diketoindole intermediates, prepared by Friedel-Crafts acylations of 3-substituted indoles, have been converted to 3-hydroxycarbazoles and β-carbolines in good yields, 51-96% and 82-97%, respectively. This method also allows for the formation of 4-substituted β-carbolines. The application of this methodology to the synthesis of the natural products hyellazole and 6-chlorohyellazole is also described.
Total Syntheses of Carazostatin, Hyellazule, and Carbazoquinocins B-F
Choshi, Tominari,Sada, Takuya,Fujimoto, Hiroyuki,Nagayama, Chizu,Sugino, Eiichi,Hibino, Satoshi
, p. 2535 - 2543 (2007/10/03)
Total syntheses of carazostatin (1), hyellazole (2a), and carbazoquinocins B-F (3b-f) have been completed. The cross-coupling reaction between 3-iodoindole 8 and vinylstannane 11b gave the 3-alkenylindole 7. Treatment of 7 with ethynylmagnesium bromide, followed by etherification of the resulting alcohol 12 with MOMCl, yielded the 3-alkenyl-2-propargylindole 6. The compound 6 was treated with t-BuOK in t-BuOH at 90°C to obtain the desired carbazoles 4 together with the N-deprotected carbazole 13 through an allene-mediated electrocyclic reaction. The carbazole 13a, derived from 4a or 4c, was converted into the triflate 24 in two steps. The triflate 24 was subjected to the Suzuki cross-coupling reaction with either 9-heptyl-9-BBN or phenylboronic acid in the presence of a palladium catalyst to produce the 1-heptylcarbazole 25a and the 1-phenylcarbazole 25b. Cleavage of the ether bond of 25a yielded carazostatin (1). Cleavage of the ether bond of 25b followed by O-methylation gave hyellazole (2a). Oxidation of carazostatin (1) with benzene seleninic anhydride afforded carbazoquinocin C (3c). In a similar way, carbazoquinocins B and D-F (3b,d-f) were synthesized, respectively.
Total synthesis of carazostatin and hyellazole by allene-mediated electrocyclic reaction
Choshi,Sada,Fujimoto,Nagayama,Sugino,Hibino
, p. 2593 - 2596 (2007/10/03)
The free radical scavenger carazostatin and the marine alkaloid hyellazole have been synthesized by a new type of allene-mediated electrocyclic reaction involving the indole 2,3-bond as a key step.
Synthesis of the Carbazole Alkaloids Carbazomycin A and B and Hyellazole
Moody, Christopher J.,Shah, Pritom
, p. 376 - 377 (2007/10/02)
The first synthesis of carbazomycins A and B (1) is described; the route involves Diels-Alder reaction of 1-methylpyranoindol-3-one with ethyl 3-trimethylsilylpropynoate followed by functional group interconversions; the marine alkaloid hyellazole
