100571-64-0

Basic information

• Product Name: 3-(2-isocyanoethyl)-1H-indole
• Synonyms: 3-(2-isocyanoethyl)-1H-indole;1H-Indole, 3-(2-isocyanoethyl)-
• CAS NO: 100571-64-0
• Molecular Formula: C₁₁H₁₀N₂
• Molecular Weight: 170.214
• Mol File: 100571-64-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-(2-isocyanoethyl)-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-isocyanoethyl)-1H-indole(100571-64-0)
• EPA Substance Registry System: 3-(2-isocyanoethyl)-1H-indole(100571-64-0)

Safety Data

• Hazardous Substances Data: 100571-64-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
3-(2-Isocyanoethyl)-1H-indole is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a building block for the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 3-(2-Isocyanoethyl)-1H-indole is used as a compound of interest for its potential biological activities. Researchers explore its properties to understand how it can be utilized in the creation of novel therapeutic agents.
Used in Chemical Process Development:
3-(2-Isocyanoethyl)-1H-indole is also used in the development of new chemical processes. Its versatility as a compound makes it a valuable asset in the search for more efficient and innovative methods in chemical synthesis.
Used in Chemical Biology Research:
3-(2-Isocyanoethyl)-1H-indole has been investigated for its potential as a fluorescent probe in chemical biology research. Its properties may allow it to be used in the study of biological processes, offering insights into cellular mechanisms and interactions.

Upstream product

• 593-75-9 methyl isocyanate 
• 5457-31-8 (3-indolylmethyl)trimethylammonium iodide 
• 95-20-5 2-methyl-1H-indole 
• 487-89-8 Indole-3-carboxaldehyde 
• 3156-51-2 3-(2-nitroethenyl)-1H-indole 
• 61-54-1 tryptamine 
• 6502-82-5 N_b-formyltryptamine 

Downstream Products

• 1447343-90-9 (2S)-2-((1-(2-(1H-indol-3-yl)ethyl)-3-methyl-2,5-dioxopyrrolidin-3-yl)amino)-N-isopropyl-3-phenylpropanamide 

Relevant articles and documents

Hydrogen-Bonding-Promoted Cascade Rearrangement Involving the Enlargement of Two Rings: Efficient Access to Polycyclic Quinoline Derivatives

An efficient cascade reaction of tryptamine-derived isocyanides with C,N-cyclic azomethine imines is described. The polycyclic pyrrolo[2,3-c]quinoline derivatives, which benefited from rearrangement process driven by hydrogen bonding, could be directly assembled in moderate to good yields (40–87 %) under metal-free and mild conditions. This transformation involved four new heterocyclic rings formations and uniquely, ring opening of indole as well as ring expansion of C,N-cyclic azomethine imine. Both experimental and DFT studies provided guidance on the in-depth insight into the reaction pathways and hydrogen bonding was identified to lower the free energy barrier in transition states. This work constitutes a rare example of tryptamine-derived isocyanide-based cascade reactions, and potentially could be a powerful synthetic strategy for accessing polycyclic analogues involved in natural products.

Synthesis of polycyclic spiroindolines by highly diastereoselective interrupted Ugi cascade reactions of 3-(2-isocyanoethyl)indoles

We report a highly diastereoselective interrupted Ugi reaction to construct a broad range of structurally congested and stereochemically complex spiroindolines from tryptamine-derived isocyanides. The reaction is facilitated by using fluorinated alcohols (TFE or HFIP) as solvents and tolerates a broad range of amines, aldehydes and 2-isocyanoethylindoles to give polycyclic products in moderate to excellent yields.

A Convergent Approach to Heterocycle Synthesis via Silver Ion Mediated α-Keto Imidoyl Halide-Arene Cyclizations. An Application to the Synthesis of the Erythrinane Skeleton

α-Keto imidoyl halides formed by the reaction of representative 2-phenylethyl and related isocyanides with acyl halides undergo facile cyclization induced by silver salts to provide the corresponding heterocycles in good to excellent yield.An efficient synthesis of the erythrinane skeletal system which relies upon the sequential utlization of this method followed by an azomethine ylide cycloaddition reaction is described.

Iodospirocyclization of Tryptamine-Derived Isocyanides: Formal Total Synthesis of Aspidofractinine

The N-iodosuccinimide-mediated spirocyclization of tryptamine-derived isocyanides to generate spiroindolenines is reported. The products contain both an imine and an imidoyl iodide as flexible handles for follow-up chemistry. Nucleophilic addition typical

Visible-Light-Induced Trifluoromethylation of Isonitrile-Substituted Indole Derivatives: Access to 1-(Trifluoromethyl)-4,9-dihydro-3H-pyrido[3,4-b]indole and β-Carboline Derivatives

A visible-light-induced trifluoromethylation of isonitrile-substituted indole derivatives has been developed from the reaction of isonitrile-substituted indoles with Togni II reagent, affording 1-(trifluoromethyl)-4,9-dihydro-3H-pyrido[3,4-b]indoles in mo

Synthesis of Oxazolidin-2-ones by Oxidative Coupling of Isonitriles, Phenyl Vinyl Selenone, and Water

Reaction of alkyl isocyanides, phenyl vinyl selenone, and water in the presence of a catalytic amount of Cs2CO3 afforded oxazolidin-2-ones in good yields. This unprecedented heteroannulation process created four chemical bonds in a s

Asymmetric dearomatization of indoles through a Michael/Friedel-Crafts-Type cascade to construct polycyclic spiroindolines

A highly efficient asymmetric dearomatization of indoles was realized through a cascade reaction between 2-isocyanoethylindole and alkylidene malonates catalyzed by a chiral N,N-dioxide/MgII catalyst. Fused polycyclic indolines containing three stereocenters were afforded in good yields with excellent diastereo- and enantioselectivities through a Michael/Friedel-Crafts/Mannich cascade. When 2-substituted 2-isocyanoethylindoles were used, spiroindoline derivatives were obtained through a Michael/Friedel-Crafts reaction.

Continuous-flow synthesis of thioureas, enabled by aqueous polysulfide solution

We have developed the continuous-flow synthesis of thioureas in a multicomponent reaction starting from isocyanides, amidines, or amines and sulfur. The aqueous polysulfide solution enabled the application of sulfur under homogeneous and mild conditions. The crystallized products were isolated by simple filtration after the removal of the co-solvent, and the sulfur retained in the mother liquid. Presenting a wide range of thioureas synthesized by this procedure confirms the utility of the convenient continuous-flow application of sulfur.

Isocyanide 2.0

The isocyanide functionality due to its dichotomy between carbenoid and triple bond characters, with a nucleophilic and electrophilic terminal carbon, exhibits unusual reactivity in organic chemistry exemplified for example in the Ugi reaction. Unfortunately, the over proportional use of only a few isocyanides hampers novel discoveries about the fascinating reactivity of this functional group. The synthesis of a broad range of isocyanides with multiple functional groups is lengthy, inefficient, and exposes the chemist to hazardous fumes. Here we present an innovative isocyanide synthesis overcoming these problems by avoiding the aqueous workup which we exemplify by parallel synthesis from a 0.2 mmol scale performed in 96-well microtiter plates up to a 0.5 mol multigram scale. The advantages of our methodology include an increased synthesis speed, very mild conditions giving access to hitherto unknown or highly reactive classes of isocyanides, rapid access to large numbers of functionalized isocyanides, increased yields, high purity, proven scalability over 5 orders of magnitude, increased safety and less reaction waste resulting in a highly reduced environmental footprint. For example, the hitherto believed to be unstable 2-isocyanopyrimidine, 2-acylphenylisocyanides and even o-isocyanobenzaldehyde could be accessed on a preparative scale and their chemistry was explored. Our new isocyanide synthesis will enable easy access to uncharted isocyanide space and will result in many discoveries about the unusual reactivity of this functional group. This journal is

Efficient syntheses and anti-cancer activity of xenortides A-D including: Ent / epi -stereoisomers

A one-pot, two-step, total synthesis of naturally occurring xenortides A, B, C and D, (Xens A-D) isolated from the bacterium Xenorhabdus nematophila, and an entire complementary set of stereoisomers, has been achieved. Compounds were synthesized utilizing an isocyanide-based Ugi 4-CR followed by facile N-Boc deprotection. The reaction sequence took advantage of the chiral pool of N-Boc protected amino acids (l-Leu/Val and d-Leu/Val) with aryl isocyanides, phenyl acetaldehyde and methylamine giving the desired Xens A-D (A and B >98% ee) and all subsequent stereoisomers in reasonable yields upon deprotection followed by separation of diastereomers. Also, detailed mechanistic insights for diastereoselectivity of (-)-Xen A, as a model in the Ugi 4-CR, has been described. Moreover, for the first time, this focused library was screened for cytotoxicity against a panel of epithelial cancer cell lines as well as normal cell lines with an MTT proliferation assay. The structure-activity relationship (SAR) study demonstrated that tryptamides Xen B and D were more active than phenylethylamides Xen A and C. Furthermore, (-)-Xen B (IC50 = 19-25 μM) and ent-(+)-Xen D (IC50 = 21-26 μM) gave the highest cytotoxicity and they were also found to be non-toxic toward normal cells. Importantly, the SAR results indicate that the stereochemistry at C8 and C11 in (-)-Xen B and ent-(+)-Xen D play a critical role in cytotoxic activity.