74117-31-0

Upstream product

• 120-72-9 indole 
• 1885-14-9 phenyl chloroformate 
• 139-02-6 sodium phenoxide 
• 109241-96-5 indole-1-carboxylic acid anhydride 
• 530-62-1 1,1'-carbonyldiimidazole 
• 108-95-2 phenol 
• 13884-13-4 indole-1-carboxylic acid 
• 102-09-0 bis(phenyl) carbonate 

Downstream Products

• 140887-32-7 (3aS,3bS,8aS,8bR)-2,3,3a,3b,8a,8b-Hexahydro-1H-8-aza-cyclopenta[3,4]cyclobuta[1,2-a]indene-8-carboxylic acid phenyl ester 
• 140887-32-7 (3aR,3bS,8aS,8bS)-2,3,3a,3b,8a,8b-Hexahydro-1H-8-aza-cyclopenta[3,4]cyclobuta[1,2-a]indene-8-carboxylic acid phenyl ester 

Relevant academic research and scientific papers

An easy-to-operate n-carbonylation of indoles with diaryl carbonates as reagent and Na2CO3 as catalyst

Na2CO3 catalyzed N-carbonylation of indoles using diaryl carbonates as acylation reagent have been developed. It provided an efficient and simple method for the utilization of carbonates and the synthesis of N-carbonyl indoles. The reaction can be operated easily with Na2CO3 as catalyst in CH3CN and the corresponding products were isolated with good to excellent yields.

Carbonic acid diester activation by polymer-bound DBU and its relevance to catalytic N-carbonylation of N-heteroaromatics: Direct evidence for an elusive N-carboxy-substituted amidinium cation intermediate

Polymer-bound DBU (PS-DBU, DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene) is an effective and selective catalyst for solventless N-phenoxycarbonylation of N-heteroaromatics (pyrrole (1), indole (2), and carbazole (3)) with diphenyl carbonate (DPC), used as an

A simple direct phosgeneless route to N-heteroaryl unsymmetrical ureas

A new simple approach to the synthesis of unsymmetrical ureas HetNC(O)NRR′ (HetNH = pyrrole, indole, carbazole; R, R′ = H, alkyl, aryl) has been explored, which involves the direct reaction of the N-phenoxycarbonyl derivatives of pyrrole, indole and carba

Solventless selective phosgene-free N-carbonylation of N-heteroaromatics (pyrrole, indole, carbazole) under mild conditions

N-Heteroaromatics HetNH, such as pyrrole (1), indole (2) and carbazole (3), have been selectively N-carbonylated by a direct reaction with diphenyl carbonate (DPC), used as an environmental friendly carbonyl active species in place of toxic and hazardous phosgene. The carbonylation reaction can be effectively catalyzed by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), which can act as a base catalyst by activating the HetNH substrate, and as a nucleophile catalyst by activating the organic carbonate. The influence of reaction parameters (temperature, reaction time, DBU load, DPC/HetNH molar ratio) on the productivity of the process has been also investigated. The synthetic methodology does not require severe temperature conditions, is solventless, simple (only one step), efficient and selective, and offers a new solution to the synthesis of synthetically versatile HetNCO2Ph derivatives through a route alternative to the current traditional phosgenation methods.

Superbase-promoted direct N-carbonylation of pyrrole with carbonic acid diesters

Carbonic acid diesters have been investigated as carbonylating agents in the direct reaction with pyrrole (HetNH). In the presence of superbases (DBU, P1-t-Bu, BTPP) as catalysts, the heteroaromatic substrate can be N-carbonylated by direct reaction with carbonic acid diesters under not-severe experimental conditions. The carbonylation reaction makes accessible pyrrole N-carbonyl derivatives (HetNC(O)OR, (HetN)2CO) selectively through a simple straightforward way, which offers a safe eco-friendly alternative to the traditional synthetic methods based on hazardous phosgene or phosgene-derivatives.

Mild and selective deprotection of carbamates with Bu4NF

A new mild method allowing the removal of carbamates using TBAF in THF is reported. Reactions were performed on indole, indoline, N-methyl aniline, aniline and tryptamine derivatives. The observed selectivity according to the carbamates or the substrates is discussed. A mechanism is postulated. Graphical Abstract

Neutral acylation (protection) of the indole nitrogen: A simple synthesis of indole-1-carboxylates, indole-1-thiocarboxylates and indole-1- carboxamides

A simple synthesis of indole-1-carboxylates, indole-1-thiocarboxylates and indole-1-carboxamides (1) under neutral conditions is described.

Removable groups for activation of indole photochemistry

The ability of a series of nitrogen-substituents to activate the cycloaddition photochemistry of indoles has been examined; the N-substitutents were chosen in order to enable their removal following cycloaddition under mild neutral, acidic or basic condit

OXIDATION OF 1-BENZOYLPYRROLE AND 1-AROYLINDOLES BY PALLADIUM ACETATE

Oxidation of 1-benzoylpyrrole and 1-aroylindoles by palladium acetate in acetic acid gave the corresponding ring-closed products and dimerized compounds.