DBU-Catalyzed Alkyne–Imidate Cyclization toward 1-Alkoxypyrazino[1,2-<i>a</i>]indole Synthesis

Festa, Alexey А.; Zalte, Rajesh R; Голанцов, Никита Е.; Варламов, А. В.; Eycken, Erik V. Van der; Voskressensky, Leonid G.

doi:10.1021/acs.joc.8b01279

Cited by 19 publications

(18 citation statements)

References 42 publications

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“…On the basis of these experimental results, a possible reaction mechanism was proposed using the synthesis of 3a as an example, as shown in Scheme . In the presence of a base, 2a is converted into alkoxy anion intermediate I , which is easily reacted with 1a through nucleophilic addition to give intermediate II . The latter then gives the intermediate benzyl pyrimidine‐2‐carbimidate ( 3a′ ) by capturing H + .…”

Section: Resultsmentioning

confidence: 99%

Decyanative Cross‐Coupling of Cyanopyrimidines with O‐, S‐, and N‐Nucleophiles: A Route to Alkoxylpyrimidines, Aminopyrimidines and Alkylthiopyrimidines

et al. 2019

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The transition metal‐free cross‐coupling reactions of cyanopyrimidines with aliphatic alcohols, thiols (or S‐alkylisothiourea salts) and amines, giving the corresponding alkoxylpyrimidines, aminopyrimidines, and alkylthiopyrimidines, are reported. Preliminary mechanistic studies reveal that it probably involves a sequential nucleophilic addition‐intramolecular rearrangement process, which is promoted by an intramolecular N–H···N five‐membered hydrogen bonding interaction. The presence of a nitrogen atom next to the cyano group is indispensable. The wide substrate scope with excellent yields makes cyanopyrimidines a promising alternative substrate class to the frequently used pyrimidines halides for the formation of C–O, C–S, and C–N bonds through the decyanative cross‐coupling reaction.

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Section: Resultsmentioning

confidence: 99%

Decyanative Cross‐Coupling of Cyanopyrimidines with O‐, S‐, and N‐Nucleophiles: A Route to Alkoxylpyrimidines, Aminopyrimidines and Alkylthiopyrimidines

et al. 2019

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“…on C2 with a nucleophile linked to the indole nitrogen atom, thus creating the pyrazino C-ring ( Scheme 1 ). For example, 2-substituted-1-(prop-2-yn-1-yl)-1 H -indoles 5 , 7 , 9 , 11 , 13 transformed into pyrazinoindoles 6 , 8 , 10 , 12 and 14 respectively by intramolecular cyclization using NH 3 in MeOH, [ 9 , 10 ] DBU under microwave irradiation, [ 11 ] AuCl 3 [ 12 ] as triple bond activator, Ni(OAc) 2 in the presence of hydroxylamine [ 13 ] or NaH in DMF [ 14 ].…”

Section: Pyrazinoindoles A: Synthesis and Biological Propertiesmentioning

confidence: 99%

Synthesis and Biological Activities of Pyrazino[1,2-a]indole and Pyrazino[1,2-a]indol-1-one Derivatives

et al. 2021

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This review concerns the synthesis and biological activities of pyrazino[1,2-a]indoles and pyrazino[1,2-a]indol-1-ones reported since 1997 and the discovery of biological activity of pyrazinoindole derivatives. In the first part, we first presented the synthetic routes that have been reported from a methodological point of view to access the pyrazinoindole unit according to cyclization reactions using or not using metal catalysts. Then, syntheses and neuropsychiatric, auto-immune, anti-infectious and anti-cancer properties of pyrazinoindoles were detailed. In the second part, we first reported the main accesses to pyrazinoindol-1-one substrates according to Michael reactions, metal-catalyzed and metal-free cyclization reactions. The syntheses and anti-cancer, anti-infectious, anti-allergenic and neuropsychiatric properties of pyrazinoindolones were next described and discussed.

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“…The indole scaffold represents probably one of the most important structural subunits for the discovery of new drug candidates [6][7][8][9]. In particular, the derivatives of 2-cyanoindoles gained considerable attention in recent years because of their great importance in biological sciences, and they are also of interest thanks to this nitrile function [10][11][12]. The 2-cyanoindole unit is an example of structural motif building blocks and effective precursors for the synthesis of various indole-fused polycycles [13][14][15][16][17][18][19], substituted 2-cyanoindoles [20][21][22][23][24], addition to nitriles [25,26] and indole heterocycle substitution [27,28].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New Highly Functionalized 1H-Indole-2-carbonitriles via Cross-Coupling Reactions

et al. 2021

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An approach for the preparation of polysubstituted indole-2-carbonitriles through a cross-coupling reaction of compounds 1-(but-2-ynyl)-1H-indole-2-carbonitriles and 1-benzyl-3-iodo-1H-indole-2-carbonitriles is described. The reactivity of indole derivatives with iodine at position 3 was studied using cross-coupling reactions. The Sonogashira, Suzuki–Miyaura, Stille and Heck cross-couplings afforded a variety of di-, tri- and tetra-substituted indole-2-carbonitriles.

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DBU-Catalyzed Alkyne–Imidate Cyclization toward 1-Alkoxypyrazino[1,2-a]indole Synthesis

Cited by 19 publications

References 42 publications

Decyanative Cross‐Coupling of Cyanopyrimidines with O‐, S‐, and N‐Nucleophiles: A Route to Alkoxylpyrimidines, Aminopyrimidines and Alkylthiopyrimidines

Decyanative Cross‐Coupling of Cyanopyrimidines with O‐, S‐, and N‐Nucleophiles: A Route to Alkoxylpyrimidines, Aminopyrimidines and Alkylthiopyrimidines

Synthesis and Biological Activities of Pyrazino[1,2-a]indole and Pyrazino[1,2-a]indol-1-one Derivatives

Synthesis of New Highly Functionalized 1H-Indole-2-carbonitriles via Cross-Coupling Reactions

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