BF3 etherate-mediated microwave-assisted facile synthesis of thiopyrano[2,3-b]indol-2-one

Jha, Mukund; Davis, Connor; Fazzari, Julia; Vitali, Mario

doi:10.1016/j.tetlet.2014.10.131

Cited by 13 publications

(7 citation statements)

References 25 publications

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“…Various functional groups of substrates were compatible with this [3 + 3] annulation, delivering the corresponding products in acceptable yields. [49] Substrate scope investigation showed that high reaction temperature (180 °C) and Zn(OTf) 2 additive were necessary in the case of ethyl 2-methyl-3-oxobutanoate to obtain the corresponding products.…”

Section: Inorganic Base-mediated Annulationmentioning

confidence: 99%

“…Jha and co‐workers reported a Pechmann‐type condensation reaction of indoline‐2‐thiones 58 and acetoacetic esters 127 to synthesize indole‐annulated 2 H ‐thiopyran‐2‐ones 128 in the presence of BF 3 ⋅ OEt 2 under microwave irradiation (Scheme 33). Various functional groups of substrates were compatible with this [3+3] annulation, delivering the corresponding products in acceptable yields [49] . Substrate scope investigation showed that high reaction temperature (180 °C) and Zn(OTf) 2 additive were necessary in the case of ethyl 2‐methyl‐3‐oxobutanoate to obtain the corresponding products.…”

Section: ‐Thioxoindolines As Starting Materialsmentioning

confidence: 99%

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Construction of Indole‐Fused Heterocycles Starting from 2‐Thioxoindolines, Iminoindolines, and Their Derivatives

Zhao

Gou

et al. 2021

Adv Synth Catal

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Indole-based heterocycles containing sulfur or nitrogen atoms are important frameworks that occur widely in biological active natural products and drugs. Consequently, several novel chemical transformations and new catalytic strategies have been developed for the preparation of these skeletons in a highly efficient and selective manner. This review focuses on recent advancements in the construction of indole-fused heterocyclic compounds by using iminoindolines, 3-diazoindol-2-imines, 2-thioxoindolines, and their derivatives as starting materials.

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Section: Inorganic Base-mediated Annulationmentioning

confidence: 99%

Section: ‐Thioxoindolines As Starting Materialsmentioning

confidence: 99%

Construction of Indole‐Fused Heterocycles Starting from 2‐Thioxoindolines, Iminoindolines, and Their Derivatives

Zhao

Gou

et al. 2021

Adv Synth Catal

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“…21 We have a long-standing interest in the synthesis of functionalized indoles. [22][23][24][25][26] Given the low thermal stability of sulfides 11, we envisaged that they would be more conducive to milder base-assisted hydroamination conditions to furnish N-fused heterocycles. Towards that end, herein, we report a general, metal-free, mild and efficient method for the synthesis of thiazolo[3,2-a]indoles 14 exploiting the reactivity 2-(prop-2-ynylthio)-1H-indoles 11.…”

Section: Syn Thesismentioning

confidence: 99%

Metal-Free Hydroamination of Alkynes: A Mild and Concise Synthesis of Thiazolo[3,2-a]indoles and their Cytotoxic Activity

et al. 2019

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“…Derivatives of thiopyran, and thiopyrano-fused pyrazoles and other heterocycles, on the other hand, constitute a class of sulfur heterocycle analogs of the possessing significant bioactivities [16][17][18][19][20]. RP 49356 is a K + channel opener [17].…”

Section: Introductionmentioning

confidence: 99%

One-pot synthesis, biological evaluation, and docking study of new chromeno-annulated thiopyrano[2,3-c]pyrazoles

et al. 2016

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A one-pot synthesis of new chromeno-annulated thiopyrano[2,3-c]pyrazoles has been achieved through a domino-Knoevenagel-hetero-Diels-Alder reaction after combining various pyrazol-5-thiones with O-alkenyloxy/alkynyloxy-salicylaldehydes/naphthaldehydes in a Brønsted acidic ionic liquid, [Hmim]HSO[Formula: see text], methylimidazolium hydrogen sulphate, under microwave irradiation. The method is simple and in many cases the isolated products did not require further purification. The central pyranothiopyranyl cis-fusion was confirmed by 2D NMR NOESY and single-crystal X-ray analysis suggesting that the endo-E-Syn transition state would be the most favored pathway of the reaction. Many heterocycles of this new series were found active against six bacterial and two fungal strains. In addition, all the compounds possess good anti-oxidant activity with the ferric reducing anti-oxidant power value [Formula: see text]. All new structures were docked into active site of angiotensin I converting enzyme (ACE), assuming that the compounds possessed the anti-hypertensive activity potential on the basis of prediction of activity spectra of substances prediction results. Pyranyl ring oxygen in compound 9a forms two hydrogen bonds with HIS353 and HIS513 residues in the active site of the ACE having good G score ([Formula: see text]) of this compound, comparable to that of the reference drug captopril ([Formula: see text]).

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BF3 etherate-mediated microwave-assisted facile synthesis of thiopyrano[2,3-b]indol-2-one

Cited by 13 publications

References 25 publications

Construction of Indole‐Fused Heterocycles Starting from 2‐Thioxoindolines, Iminoindolines, and Their Derivatives

Construction of Indole‐Fused Heterocycles Starting from 2‐Thioxoindolines, Iminoindolines, and Their Derivatives

Metal-Free Hydroamination of Alkynes: A Mild and Concise Synthesis of Thiazolo[3,2-a]indoles and their Cytotoxic Activity

One-pot synthesis, biological evaluation, and docking study of new chromeno-annulated thiopyrano[2,3-c]pyrazoles

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