19/10/2022 - Page 2 of 6 - Indole Building Blocks

Wu, Wanqing’s team published research in Organic Chemistry Frontiers in 2019 | CAS: 399-52-0

5-Fluoro-1H-indole(cas: 399-52-0) is a member of aromaticfluorinated building blocks. Fluorine-containing aromatics have been incorporated into crop-protection chemicals (herbicides, insecticides, fungicides). Liquid crystals, positron emission tomography, and imaging systems represent new areas where fluoroaromatics and fluoroheterocyclics have gained attention.Formula: C8H6FN

The author of 《Palladium-catalyzed regioselective C-H alkynylation of indoles with bromoalkynes in water》 were Wu, Wanqing; Fang, Songjia; Jiang, Guangbin; Li, Meng; Jiang, Huanfeng. And the article was published in Organic Chemistry Frontiers in 2019. Formula: C8H6FN The author mentioned the following in the article:

A highly regioselective alkynylation of indoles was accomplished for the assembly of functionalized C2 alkynyl indoles in moderate to good yields with a primary amine as the directing group. This protocol represented an efficient palladium-catalyzed C(sp2)-H activation/alkynylation using water/aqueous media as a sustainable solvent. Moreover, the scalability was demonstrated and further transformations of the alkynylating products were achieved, demonstrated the potential applications in synthetic and pharmaceutical chem. Preliminary mechanistic investigations suggested that the cleavage of the C2 C-H bond of indoles was likely to be the rate-determining step in this reaction. The experimental part of the paper was very detailed, including the reaction process of 5-Fluoro-1H-indole(cas: 399-52-0Formula: C8H6FN)

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

Wu, Jiaping’s team published research in Organic Chemistry Frontiers in 2021 | CAS: 399-52-0

Wu, Jiaping; Qian, Baiyang; Lu, Lili; Yang, Haitao; Shang, Yongjia; Zhang, Jitan published their research in Organic Chemistry Frontiers in 2021. The article was titled 《Access to the C2 C-H olefination, alkylation and deuteration of indoles by rhodium(III) catalysis: an opportunity for diverse syntheses》.Recommanded Product: 399-52-0 The article contains the following contents:

A concise approach for the synthesis of structurally diverse indoles enabled by RhIII-catalyzed switchable C2 C-H olefination and alkylation of N-quinolinyl indoles with alkenes as well as highly efficient C-H deuteration was described. The reaction could be conducted under practical reaction conditions, with a broad substrate scope and good tolerance of various functional groups. The potential value of this synthetic methodol. was shown by the diverse late-stage modification of the products, thereby providing a straightforward route to access functionalized indoles, especially indole-based P,N ligands. In addition to this study using 5-Fluoro-1H-indole, there are many other studies that have used 5-Fluoro-1H-indole(cas: 399-52-0Recommanded Product: 399-52-0) was used in this study.

Zeng, Miao’s team published research in Journal of Organic Chemistry in 2021 | CAS: 399-52-0

Zeng, Miao; Xue, Jing-Wen; Jiang, Hongwu; Li, Kaiwen; Chen, Yunong; Chen, Zhuqi; Yin, Guochuan published their research in Journal of Organic Chemistry in 2021. The article was titled 《Decarboxylative Addition of Propiolic Acids with Indoles to Synthesize Bis(indolyl)methane Derivatives with a Pd(II)/LA Catalyst》.Product Details of 399-52-0 The article contains the following contents:

The present work introduces a Pd(II)/LA-catalyzed (LA: Lewis acid) decarboxylative addition reaction for the synthesis of bis(indolyl)methane derivatives The presence of Lewis acid such as Sc(OTf)3 triggered Pd(II)-catalyzed decarboxylative addition of propiolic acids with indoles to offer the bis(indolyl)methane derivatives in moderate to good yields, whereas neither Pd(II) nor Lewis acid alone was active for this synthesis. The catalytic efficiency of Pd(OAc)2 was highly dependent on the Lewis acidity of the added Lewis acid, i.e., a stronger Lewis acid provided a higher yield of the bis(indolyl)methane derivatives Meanwhile, this Pd(II)/LA-catalyzed decarboxylative addition reaction showed good tolerance toward versatile electron-rich or -deficient substituents on the indole skeleton and on the benzyl ring of propiolic acids. The studies on the in situ 1H NMR kinetics of this Pd(II)/Sc(III) catalysis disclosed the formation of a transient vinyl-Pd(II)/Sc(III) intermediate generated by the pyrrole addition to the alkynyl-Pd(II)/Sc(III) species after decarboxylation, which was scarcely observed before. In the experiment, the researchers used many compounds, for example, 5-Fluoro-1H-indole(cas: 399-52-0Product Details of 399-52-0)

Leveille, Alexandria N.’s team published research in Organic Letters in 2021 | CAS: 399-52-0

Leveille, Alexandria N.; Echemendia, Radell; Mattson, Anita E.; Burtoloso, Antonio C. B. published their research in Organic Letters in 2021. The article was titled 《Enantioselective Indole Insertion Reactions of α-Carbonyl Sulfoxonium Ylides》.Safety of 5-Fluoro-1H-indole The article contains the following contents:

The first example of organocatalytic enantioselective C-H insertion reactions of indoles and sulfoxonium ylides is reported. Under the influence of phosphoric acid catalysis, levels of enantiocontrol in the range of 20-93% ee and moderate yields (up to 50%) were achieved for 29 examples in formal C-H insertion reactions of indoles and α-carbonyl sulfoxonium ylides. No nitrogen protection on the indole is necessary. The experimental part of the paper was very detailed, including the reaction process of 5-Fluoro-1H-indole(cas: 399-52-0Safety of 5-Fluoro-1H-indole)

Naaz, Fatima’s team published research in Future Medicinal Chemistry in 2021 | CAS: 120-72-9

1H-Indole(cas: 120-72-9) belongs to indole. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Application of 120-72-9

Application of 120-72-9In 2021 ,《Indole derivatives (2010-2020) as versatile tubulin inhibitors: synthesis and structure-activity relationships》 appeared in Future Medicinal Chemistry. The author of the article were Naaz, Fatima; Neha, Kumari; Haider, Rafi Md; Shafi, Syed. The article conveys some information:

A review. Tubulin inhibitors are conjugates that interfere with the dynamic equilibrium of the polymerization and depolymerization of microtubules. Among all the reported conjugates, indole moiety is one of the most significant classes for the development of new drug candidates for cancer therapy. Due to their presence in a wide range of natural as well as synthetic antitubulin agents, indole has become a versatile scaffold in research, and various synthetic and semisynthetic indole-based antitubulin agents have been identified and reported. The present article focuses on the reported indole-based tubulin inhibitors of synthetic origin from last the decade. Synthesis, structure-activity relationships and biol. activities of synthetic indole derivatives along with brief updates on their antitubulin activity are presented. The experimental process involved the reaction of 1H-Indole(cas: 120-72-9Application of 120-72-9)

Hou, Shu Jie’s team published research in Chinese Chemical Letters in 2005 | CAS: 99409-32-2

Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2) belongs to indole.The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades.SDS of cas: 99409-32-2They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.

SDS of cas: 99409-32-2On May 31, 2005, Hou, Shu Jie; Zou, Chuan Chun; Lei, Ping Sheng; Yu, De Quan published an article in Chinese Chemical Letters. The article was 《An efficient way for glycosylation of spirostanol》. The article mentions the following:

Using thioglycosides as donors and trimethylsilyl trifluoromethanesulfonate (TMSOTf) and N-iodosuccinimide (NIS) as promoter, a modified procedure for the glycosylation of spirostanols was developed. A series of saponins were synthesized in mild condition with excellent yields. E.g., sapogenin glucoside I (R = phthalimido) was prepared with quant. yield by reacting diosgenin with Et 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside using TMSOTf, NIS and 4Å mol. sieves in CH2Cl2 at -15°. In the experimental materials used by the author, we found Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2SDS of cas: 99409-32-2)

Classon, Bjoern’s team published research in Carbohydrate Research in 1991 | CAS: 99409-32-2

Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2) belongs to indole.The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades.Category: indole-building-blockThey are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.

Category: indole-building-blockOn September 2, 1991 ,《Synthesis of an artificial antigen that corresponds to a disaccharide repeating unit of the capsular polysaccharide of Haemophilus influenzae type d. A facile synthesis of methyl 2-acetamido-2-deoxy-β-D-mannopyranoside》 was published in Carbohydrate Research. The article was written by Classon, Bjoern; Garegg, Per J.; Oscarson, Stefan; Tiden, Anna Karin. The article contains the following contents:

The synthesis is described of p-nitrophenyl acetamido(deoxyglucopyranosyl)deoxymannopyranosiduronic acid I (R = C6H4NO2-4), corresponding to the disaccharide repeating unit of the capsular polysaccharide of Haemophilus influenzae type d, which, after conversion of the p-nitro- into a p-aminophenyl residue, may be attached to a protein to make an artificial antigen for immunol. studies. The synthesis incorporates a facile route to the 2-acetamido-2-deoxy-β-D-mannopyranosyl unit. The experimental part of the paper was very detailed, including the reaction process of Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2Category: indole-building-block)

Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2) belongs to indole.The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades.Category: indole-building-blockThey are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.

Yadav, Arun’s team published research in Journal of Organic Chemistry in 2021 | CAS: 399-52-0

Yadav, Arun; Kumar, Dileep; Mishra, Manish Kumar; Deeksha; Tripathi, Chandra Bhushan published their research in Journal of Organic Chemistry in 2021. The article was titled 《Catalytic Enantioselective Synthesis of Aryl-Methyl Organophosphorus Compounds》.Application of 399-52-0 The article contains the following contents:

A catalytic enantioselective protocol for the synthesis of aryl-Me organophosphorus compounds is reported. Utilizing a chiral phosphoric acid as a catalyst, a wide range of indole derivatives reacted with phosphorylated quinomethanes in high yield with excellent enantioselectivity. This is the first report on the application of phosphorylated quinomethanes in asym. synthesis. In the experiment, the researchers used many compounds, for example, 5-Fluoro-1H-indole(cas: 399-52-0Application of 399-52-0)

Dhara, Debashis’s team published research in Tetrahedron: Asymmetry in 2014 | CAS: 99409-32-2

Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2) belongs to indole.The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades.Formula: C22H25NO9SThey are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.

Dhara, Debashis; Mandal, Pintu Kumar; Misra, Anup Kumar published an article on February 15 ,2014. The article was titled 《Convergent synthesis of a pentasaccharide repeating unit corresponding to the cell wall O-antigen of Salmonella enterica O44》, and you may find the article in Tetrahedron: Asymmetry.Formula: C22H25NO9S The information in the text is summarized as follows:

A convergent synthetic strategy has been developed for the synthesis of a pentasaccharide fragment corresponding to the O-antigen of Salmonella enterica O44 strain. An intermediate tetrasaccharide derivative was prepared by a [2+2] block glycosylation of two disaccharide derivatives The p-methoxybenzyl (PMB) group has been used as the in situ temporary protecting group minimizing the number of functional group manipulation steps. The application of the armed-disarmed glycosylation concept reduced the number of steps in the synthetic strategy. The glycosylation steps were highly stereoselective and high yielding. In the experiment, the researchers used many compounds, for example, Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2Formula: C22H25NO9S)

Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2) belongs to indole.The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades.Formula: C22H25NO9SThey are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.

Li, Ming’s team published research in Organic & Biomolecular Chemistry in 2020 | CAS: 399-52-0

《The ruthenium(II)-catalyzed C-H olefination of indoles with alkynes: the facile construction of tetrasubstituted alkenes under aqueous conditions》 was published in Organic & Biomolecular Chemistry in 2020. These research results belong to Li, Ming; Yao, Tian-Yu; Sun, Sheng-Zheng; Yan, Ting-Xun; Wen, Li-Rong; Zhang, Lin-Bao. Recommanded Product: 5-Fluoro-1H-indole The article mentions the following:

An environmentally-friendly and facile protocol for the construction of tetrasubstituted alkenes I [R1 = H, 5-Me, 4-Cl, etc.; R2 = H, Me, Ph, etc.; R3 = R4 = Ph, 4-MeC6H4, 4-BrC6H4, etc.] was established with Ru(II)-catalyzed C-H bond functionalizations under mild conditions. The method featured the usage of readily available substrates, without external oxidants and additives, 100% atom economy, and excellent regioselectivity, thus enhancing the practicability of this protocol. Moreover, this transformation proceeded smoothly under aqueous conditions and could be extended to the gram scale. N-Methoxyamide, as a directing group (DG), played a vital role in the transformation. The experimental part of the paper was very detailed, including the reaction process of 5-Fluoro-1H-indole(cas: 399-52-0Recommanded Product: 5-Fluoro-1H-indole)