Category: 167015-84-1

Nemoto, Tetsuhiro published the artcileCatalytic Asymmetric Total Synthesis of Tangutorine, HPLC of Formula: 167015-84-1, the publication is Organic Letters (2010), 12(4), 872-875, database is CAplus and MEDLINE.

The first enantioselective total synthesis of (-)-tangutorine (I) was achieved via a Pd-catalyzed asym. allylic amination using a chiral diaminophosphine oxide (DIAPHOX) preligand as the key step.

Organic Letters published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C15H20N2O2, HPLC of Formula: 167015-84-1.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Chen, Hu published the artcileA copper-catalyzed aerobic domino process for the synthesis of isoindolin-1-ylidene derivatives, Synthetic Route of 167015-84-1, the publication is Tetrahedron (2015), 71(22), 3632-3636, database is CAplus.

A convenient and efficient copper-catalyzed aerobic cascade reaction was developed for the synthesis of the pharmacol. relevant isoindolin-1-ylidene scaffold. Various ortho-formyl cinnamates could react smoothly with different amines in the presence of a com. available copper catalyst under mild aerobic conditions. Isoindolin-1-ylidene derivatives were assembled in one pot in moderate to good yields. This method features amine annulation and double dehydrogenation, representing high at. efficiency. Its product could be further converted to the privileged isoindolinone pharmacophore.

Tetrahedron published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C15H20N2O2, Synthetic Route of 167015-84-1.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Ma, Jiajia published the artcileDirect Dearomatization of Pyridines via an Energy-Transfer-Catalyzed Intramolecular [4+2] Cycloaddition, Quality Control of 167015-84-1, the publication is Chem (2019), 5(11), 2854-2864, database is CAplus.

A catalytic, dearomative cycloaddition reaction with pyridines, e.g., I using photoinduced energy transfer catalysis has been reported, thereby advancing dearomatization methodol. and increasing the topol. of pyridine dearomatization products, e.g., II. This unprecedented method features high yields, broad substrate scope, excellent functional group tolerance, and facile scalability. Furthermore, a recyclable and sustainable polymer immobilized photocatalyst was employed. Computational and exptl. investigations support a mechanism in which a cinnamyl moiety is promoted to its corresponding excited triplet state through visible-light-mediated energy transfer catalysis, followed by a regioselective and dearomative [4+2] cycloaddition to pyridines. This work demonstrates the contribution of visible light catalysis toward enabling thermally challenging organic transformations.

Chem published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C15H20N2O2, Quality Control of 167015-84-1.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Liu, Chengjun published the artcileGold(I)-catalyzed pathway-switchable tandem cycloisomerizations to indolizino[8,7-b]indole and indolo[2,3-a]quinolizine derivatives, Formula: C15H20N2O2, the publication is Chemical Communications (Cambridge, United Kingdom) (2019), 55(96), 14418-14421, database is CAplus and MEDLINE.

Exptl. and theor. explorations were performed on the pathways of the cascade cycloisomerizations of tryptamine-N-ethynylpropiolamide substrates. The methodol. provided a common strategy to access either indolizino[8,7-b]indoles or indolo[2,3-a]quinolizines in a switchable fashion.

Chemical Communications (Cambridge, United Kingdom) published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C15H20N2O2, Formula: C15H20N2O2.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Ma, Jiajia published the artcileDirect Dearomatization of Pyridines via an Energy-Transfer-Catalyzed Intramolecular [4+2] Cycloaddition, Quality Control of 167015-84-1, the publication is Chem (2019), 5(11), 2854-2864, database is CAplus.

A catalytic, dearomative cycloaddition reaction with pyridines, e.g., I using photoinduced energy transfer catalysis has been reported, thereby advancing dearomatization methodol. and increasing the topol. of pyridine dearomatization products, e.g., II. This unprecedented method features high yields, broad substrate scope, excellent functional group tolerance, and facile scalability. Furthermore, a recyclable and sustainable polymer immobilized photocatalyst was employed. Computational and exptl. investigations support a mechanism in which a cinnamyl moiety is promoted to its corresponding excited triplet state through visible-light-mediated energy transfer catalysis, followed by a regioselective and dearomative [4+2] cycloaddition to pyridines. This work demonstrates the contribution of visible light catalysis toward enabling thermally challenging organic transformations.

Chem published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C15H20N2O2, Quality Control of 167015-84-1.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Douat-Casassus, Celine published the artcileSynthetic anticancer vaccine candidates: rational design of antigenic peptide mimetics that activate tumor-specific T-cells, Synthetic Route of 167015-84-1, the publication is Journal of Medicinal Chemistry (2007), 50(7), 1598-1609, database is CAplus and MEDLINE.

A rational design approach was followed to develop peptidomimetic analogs of a cytotoxic T-cell epitope capable of stimulating T-cell responses as strong as or stronger (heteroclytic) than those of parental antigenic peptides. The work described herein focused on structural alterations of the central amino acids of the melanoma tumor-associated antigenic peptide Melan-A/MART-1_26-35 using nonpeptidic units. A screening was first realized in silico to select altered peptides potentially capable of fitting at the interface between the major histocompatibilty complex (MHC) class-I HLA-A2 mol. and T-cell receptors (TCRs). Two compounds appeared to be high-affinity ligands to the HLA-A2 mol. and stimulated several Melan-A/MART-1 specific T-cell clones. Most remarkably, one of them even managed to amplify the response of one clone. Together, these results indicate that central TCR-contact residues of antigenic peptides can be replaced by nonpeptidic motifs without loss of binding affinity to MHC class-I mols. and T-cell triggering capacity.

Journal of Medicinal Chemistry published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C15H20N2O2, Synthetic Route of 167015-84-1.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Yang, Qing-Qing published the artcileVisible-Light-Induced Direct Photocatalytic Carboxylation of Indoles with CBr₄/MeOH, Recommanded Product: tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, the publication is Chemistry – A European Journal (2015), 21(50), 18052-18056, database is CAplus and MEDLINE.

Photocatalysis enables the cascade reactions of indoles and CBr₄ in MeOH through a C(sp²)-H functionalization/methanolysis sequence. The title reaction provides an efficient access to indole-2- and 3-carboxylates in a single operation (no preinstallation of protecting or directing groups was required) with good yields under mild reaction conditions.

Chemistry – A European Journal published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C40H35N7O8, Recommanded Product: tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Chauhan, Jyoti published the artcileBlue LED Mediated Intramolecular C-H Functionalization and Cyclopropanation of Tryptamines: Synthesis of Azepino[4, 5-b]indoles and Natural Product Inspired Polycyclic Indoles, Synthetic Route of 167015-84-1, the publication is Organic Letters (2020), 22(11), 4537-4541, database is CAplus and MEDLINE.

A novel blue LED mediated intramol. C-H functionalization of tryptamine derivatives to generate azepino[4, 5-b]indoles, e. g., I, in moderate to good yields is reported. By altering the substitution at the tryptamine nitrogen, intramol. cyclopropanation is achieved in high yields under the same reactions condition to provide natural product inspired polycyclic indoles, e. g., II, which are further transformed to spiropiperidino indoles, e. g., III, in decent yields. The mechanism of formation of the compounds was investigated through DFT studies.

Organic Letters published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C15H20N2O2, Synthetic Route of 167015-84-1.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

White, James D. published the artcileTandem Intramolecular Photocycloaddition-Retro-Mannich Fragmentation as a Route to Spiro[pyrrolidine-3,3′-oxindoles]. Total Synthesis of (卤)-Coerulescine, (卤)-Horsfiline, (卤)-Elacomine, and (卤)-6-Deoxyelacomine, Safety of tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, the publication is Journal of Organic Chemistry (2010), 75(11), 3569-3577, database is CAplus and MEDLINE.

Irradiation of a tryptamine linked through its side-chain nitrogen to an alkylidene malonate residue results in an intramol. [2 + 2] cycloaddition to the indole 2,3-double bond. The resultant cyclobutane undergoes spontaneous retro-Mannich fission to produce a spiro[indoline-3,3′-pyrrolenine] with relative configuration defined by the orientation of substituents in the transient cyclobutane. The tandem intramol. photocycloaddition-retro-Mannich process, abbreviated as TIPCARM, leads to a spiropyrrolidine which is poised to undergo a second retro-Mannich fragmentation that expels the malonate unit and generates transiently an indolenine. The latter undergoes rearrangement to a 尾-carboline, which upon brominative oxidation undergoes further rearrangement to an oxindole. With tryptamine as starting material, the entire sequence leads to the alkaloid (卤)-coerulescine (I, R = H). Starting from 5-methoxytryptamine, a parallel series affords (卤)-horsfiline I (R = MeO). Modification of the malonylidene unit to include an iso-Bu substituent at C3 affords a photosubstrate which also undergoes the TIPCARM process. In this case, a 2′-isobutyl-substituted spiro[indoline-3,3′-pyrrolenine] results. This undergoes stereoselective hydride reduction to give a product with relative orientation at the spiro carbon and the new stereocenter bearing the iso-Bu appendage corresponding to that of the alkaloid elacomine. From tryptamine, the sequence paralleling that leading to coerulescine and horsfiline terminates at 6-deoxyelacomine, whereas 6-methoxytryptamine as starting material affords (卤)-elacomine (II) itself.

Journal of Organic Chemistry published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C7H16Cl2Si, Safety of tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

White, James D. published the artcileSynthesis of the ABCD ring system of Vinca alkaloids using tandem intramolecular [2 + 2]-photocycloaddition-retro-Mannich fragmentation, HPLC of Formula: 167015-84-1, the publication is Heterocycles (2014), 88(2), 899-910, database is CAplus.

Irradiation of 3-alkylindole (E)- and (Z)-I gave spiropyrroline II via [2+2]-photocycloaddition and subsequent in situ retro-Mannich fragmentation of a fused cyclobutane. N-Alkylation of II followed by treatment of the resulting pyrrolinium salt with sodium hydride and lithium diisopropylamide generated a dienolate dianion which underwent cyclization to afford tetracyclic products, e.g., III. The configuration of III was proven by a series of NMR experiments which established that ring C in the major stereoisomer resides in a boat conformation. The prepared tetracycles contain structural features including the ABCD ring system and substituents found in certain alkaloids of the Vinca family.

Heterocycles published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C6H10O7, HPLC of Formula: 167015-84-1.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles