Tag: 161.2004

Redox-triggered dearomative [5 + 1] annulation of indoles with O-alkyl ortho-oxybenzaldehydes for the synthesis of spirochromanes was written by Cao, Lianyi;Hu, Fangzhi;Sun, Hongmei;Zhang, Xiaomei;Li, Shuai-Shuai. And the article was included in Organic Chemistry Frontiers in 2022.HPLC of Formula: 1076-74-0 This article mentions the following:

The dearomative [5 + 1] annulation of 2-methylindoles I (R = H, 4-Me, 5-F, 6-OMe, etc.) with new five-membered synthons O-alkyl ortho-oxybenzaldehydes II (R¹ = t-Bu, propan-2-yl, butan-2-yl; R² = H, Me, t-Bu; R³ = Me, ethenyl, Ph, naphthalen-2-yl, etc.; R⁴ = H, Me) was developed unprecedentedly through cascade [1,5]-hydride transfer/dearomative cyclization in HFIP for the synthesis of spirochromanes III bearing the 2-methylindolenine skeleton. In addition, the dual alkylation of the Me group of 2-methylindolenines was achieved by sequential operation through the redox neutral [5 + 1] annulation with the second five-membered synthon N-alkyl ortho-aminobenzaldehydes IV (R⁵ = Me; R⁶ = Et; R⁵R⁶ = -(CH₂)₄-; R⁷ = H, Cl), providing the chromane and tetrahydroquinoline fused spiroindolenines V in good yields. Furthermore, the auxiliary group that facilitates the hydride transfer process could be simply removed. In the experiment, the researchers used many compounds, for example, 5-Methoxy-2-methyl-1H-indole (cas: 1076-74-0HPLC of Formula: 1076-74-0).

5-Methoxy-2-methyl-1H-indole (cas: 1076-74-0) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.HPLC of Formula: 1076-74-0

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Fluorescent Indolo[3,2-a]phenazines against Toxoplasma gondii: Concise Synthesis by Gold-Catalyzed Cycloisomerization with 1,2-Silyl Migration and ipso-Iodination Suzuki Sequence was written by Merkt, Franziska K.;Mazzone, Flaminia;Sazzadeh, Shabnam Shaneh;Bonda, Lorand;Hinz, Larissa K. E.;Gruber, Irina;Buchholz, Karin;Janiak, Christoph;Pfeffer, Klaus;Mueller, Thomas J. J.. And the article was included in Chemistry – A European Journal in 2021.Related Products of 2521-13-3 This article mentions the following:

A gold-catalyzed cycloisomerization of 2-indolyl-3-[(trimethylsilyl)ethynyl)]quinoxalines with concomitant 1,2-silyl shift forms 6-(trimethylsilyl)indolo[3,2-a]phenazines in moderate to excellent yield. These silylated heterocycles are readily transformed into 6-aryl-indolo[3,2-a]phenazines in moderate to good yield by one-pot ipso-iodination Suzuki coupling. The title compounds represent a novel type of tunable luminophore. Structure-property relationships for 6-aryl-indolo[3,2-a]phenazines obtained from Hammett correlations with 蟽_p+ substituent parameters indicate that emission maxima, Stokes shifts, and fluorescence quantum yields can be fine-tuned by the remote para-aryl substituent. Furthermore, indolo[3,2-a]phenazines were found to exhibit interesting activities against medically relevant pathogens such as the Apicomplexa parasite Toxoplasma gondii with an IC₅₀ of up to 0.67卤0.13渭M. Thus, these compounds are promising candidates for novel anti-parasitic therapies. In the experiment, the researchers used many compounds, for example, 5-Methoxy-1-methyl-1H-indole (cas: 2521-13-3Related Products of 2521-13-3).

5-Methoxy-1-methyl-1H-indole (cas: 2521-13-3) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Related Products of 2521-13-3

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

C-Methylenation of anilines and indoles with CO₂ and hydrosilane using a pentanuclear zinc complex catalyst was written by Takaishi, Kazuto;Kosugi, Hiroyasu;Nishimura, Ritsuki;Yamada, Yuya;Ema, Tadashi. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2021.Category: indole-building-block This article mentions the following:

The one-step C-methylenation of anilines and indoles with CO₂ and phenylsilane was catalyzed by a pentanuclear Zn^II complex to give diarylmethanes via geminal C-H and C-C bond formation. It was proposed that the zinc-hydride complex generated in-situ was a catalytically active species and that bis(silyl)acetal was a key intermediate. When aniline was used as a substrate, both the C-methylenation and N-methylation proceeded. In the experiment, the researchers used many compounds, for example, 5-Methoxy-1-methyl-1H-indole (cas: 2521-13-3Category: indole-building-block).

5-Methoxy-1-methyl-1H-indole (cas: 2521-13-3) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Category: indole-building-block

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Ru-catalyzed oxidation and C-C bond formation of indoles for the synthesis of 2-indolyl indolin-3-ones under mild reaction conditions was written by Zhou, Xiao-Yu;Chen, Xia. And the article was included in Canadian Journal of Chemistry in 2020.Synthetic Route of C10H11NO This article mentions the following:

Herein, a ruthenium catalyzed oxidation and C-C bond formation reaction of 2-alkyl or 2-aryl substituted indoles using tert-Bu hydroperoxide (TBHP) as oxidant is described. Coupled with cascade transformation, it provided a mild catalytic oxidation system for the synthesis of 2-indolylindolin-3-ones I (R = Me, Ph, 4-FC₆H₄, etc.; R¹ = H, Me, Et; R² = 5-Me, 5-OMe, 5-Cl) . The reaction could readily occur using RuCl₃路3H₂O as catalyst, and the target product was obtained with medium to high yield. In the experiment, the researchers used many compounds, for example, 5-Methoxy-2-methyl-1H-indole (cas: 1076-74-0Synthetic Route of C10H11NO).

5-Methoxy-2-methyl-1H-indole (cas: 1076-74-0) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Synthetic Route of C10H11NO

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Cyclization of Vinylketene Dithioacetals: A Synthetic Strategy for Substituted Thiophenes was written by Pan, Ling;Zheng, Baihui;Yang, Xiaohui;Deng, Liping;Li, Yifei;Liu, Qun. And the article was included in Advanced Synthesis & Catalysis in 2021.HPLC of Formula: 1076-74-0 This article mentions the following:

A synthetic strategy for the synthesis of substituted thiophenes is described by the one-pot reaction of indoles with ketene dithioacetals under mild reaction conditions. Promoted by triflic acid (TfOH), the reaction of indoles with the easily available 伪-acetyl ketene dithioacetals resulted in the formation of vinylketene dithioacetals via condensation instead of the well known nucleophilic addition-alkylthio elimination process. In the presence of CuBr₂, vinylketene dithioacetals can cyclize into the corresponding substituted thiophenes. This transformation may benefit from the acidic reaction conditions and the steric effects of the 2-substituted indoles. In the experiment, the researchers used many compounds, for example, 5-Methoxy-2-methyl-1H-indole (cas: 1076-74-0HPLC of Formula: 1076-74-0).

5-Methoxy-2-methyl-1H-indole (cas: 1076-74-0) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.HPLC of Formula: 1076-74-0

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Redox-triggered dearomative [5 + 1] annulation of indoles with O-alkyl ortho-oxybenzaldehydes for the synthesis of spirochromanes was written by Cao, Lianyi;Hu, Fangzhi;Sun, Hongmei;Zhang, Xiaomei;Li, Shuai-Shuai. And the article was included in Organic Chemistry Frontiers in 2022.HPLC of Formula: 1076-74-0 This article mentions the following:

The dearomative [5 + 1] annulation of 2-methylindoles I (R = H, 4-Me, 5-F, 6-OMe, etc.) with new five-membered synthons O-alkyl ortho-oxybenzaldehydes II (R¹ = t-Bu, propan-2-yl, butan-2-yl; R² = H, Me, t-Bu; R³ = Me, ethenyl, Ph, naphthalen-2-yl, etc.; R⁴ = H, Me) was developed unprecedentedly through cascade [1,5]-hydride transfer/dearomative cyclization in HFIP for the synthesis of spirochromanes III bearing the 2-methylindolenine skeleton. In addition, the dual alkylation of the Me group of 2-methylindolenines was achieved by sequential operation through the redox neutral [5 + 1] annulation with the second five-membered synthon N-alkyl ortho-aminobenzaldehydes IV (R⁵ = Me; R⁶ = Et; R⁵R⁶ = -(CH₂)₄-; R⁷ = H, Cl), providing the chromane and tetrahydroquinoline fused spiroindolenines V in good yields. Furthermore, the auxiliary group that facilitates the hydride transfer process could be simply removed. In the experiment, the researchers used many compounds, for example, 5-Methoxy-2-methyl-1H-indole (cas: 1076-74-0HPLC of Formula: 1076-74-0).

5-Methoxy-2-methyl-1H-indole (cas: 1076-74-0) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.HPLC of Formula: 1076-74-0

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Fluorescent Indolo[3,2-a]phenazines against Toxoplasma gondii: Concise Synthesis by Gold-Catalyzed Cycloisomerization with 1,2-Silyl Migration and ipso-Iodination Suzuki Sequence was written by Merkt, Franziska K.;Mazzone, Flaminia;Sazzadeh, Shabnam Shaneh;Bonda, Lorand;Hinz, Larissa K. E.;Gruber, Irina;Buchholz, Karin;Janiak, Christoph;Pfeffer, Klaus;Mueller, Thomas J. J.. And the article was included in Chemistry – A European Journal in 2021.Related Products of 2521-13-3 This article mentions the following:

A gold-catalyzed cycloisomerization of 2-indolyl-3-[(trimethylsilyl)ethynyl)]quinoxalines with concomitant 1,2-silyl shift forms 6-(trimethylsilyl)indolo[3,2-a]phenazines in moderate to excellent yield. These silylated heterocycles are readily transformed into 6-aryl-indolo[3,2-a]phenazines in moderate to good yield by one-pot ipso-iodination Suzuki coupling. The title compounds represent a novel type of tunable luminophore. Structure-property relationships for 6-aryl-indolo[3,2-a]phenazines obtained from Hammett correlations with σ_p+ substituent parameters indicate that emission maxima, Stokes shifts, and fluorescence quantum yields can be fine-tuned by the remote para-aryl substituent. Furthermore, indolo[3,2-a]phenazines were found to exhibit interesting activities against medically relevant pathogens such as the Apicomplexa parasite Toxoplasma gondii with an IC₅₀ of up to 0.67±0.13μM. Thus, these compounds are promising candidates for novel anti-parasitic therapies. In the experiment, the researchers used many compounds, for example, 5-Methoxy-1-methyl-1H-indole (cas: 2521-13-3Related Products of 2521-13-3).

5-Methoxy-1-methyl-1H-indole (cas: 2521-13-3) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Related Products of 2521-13-3

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

C-Methylenation of anilines and indoles with CO₂ and hydrosilane using a pentanuclear zinc complex catalyst was written by Takaishi, Kazuto;Kosugi, Hiroyasu;Nishimura, Ritsuki;Yamada, Yuya;Ema, Tadashi. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2021.Category: indole-building-block This article mentions the following:

The one-step C-methylenation of anilines and indoles with CO₂ and phenylsilane was catalyzed by a pentanuclear Zn^II complex to give diarylmethanes via geminal C-H and C-C bond formation. It was proposed that the zinc-hydride complex generated in-situ was a catalytically active species and that bis(silyl)acetal was a key intermediate. When aniline was used as a substrate, both the C-methylenation and N-methylation proceeded. In the experiment, the researchers used many compounds, for example, 5-Methoxy-1-methyl-1H-indole (cas: 2521-13-3Category: indole-building-block).

5-Methoxy-1-methyl-1H-indole (cas: 2521-13-3) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Category: indole-building-block

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles