68557-32-4

Upstream product

• 100-63-0 phenylhydrazine 
• 98-89-5 Cyclohexanecarboxylic acid 
• 2719-27-9 cyclohexanylcarbonyl chloride 

Downstream Products

• 28669-43-4 5-cyclohexyl-3-phenyl-3H-[1,3,4]oxadiazol-2-one 
• 16537-05-6 tert-butyl cyclohexanecarboxylate 
• 188837-40-3 cyclohexanecarboxylic acid N,N'-dimethyl-N'-phenylhydrazide 
• 68051-20-7 2-cyclohexyl-1-methyl-1H-indole 
• 102804-54-6 1′-methylspiro[cyclohexane-1,3′-indolin]-2′-one 
• 4933-14-6 spiro[cyclohexane-1,3'-[3H]indol]-2'(1'H)-one 

Relevant academic research and scientific papers

Use of acylhydrazine- and acylhydrazone-type ligands to promote CuI-catalyzed C-N cross-coupling reactions of aryl bromides with N-heterocycles

A series of ten acylhydrazine- and acylhydrazone-type ligands were designed and synthesized. Their electronic and steric properties were easily modified and tuned by varying the substituents in the vicinity of the acylhydrazine and acylhydrazone units. The effect of ligands on the catalytic activity of Ullmann reactions was assessed by using a combination of these ligands with CuI. The catalytic system is very efficient for the C-N coupling reaction of azoles with aryl and heteroaryl bromides. A simple and efficient procedure for copper-catalyzed C-N cross-coupling reactions between aryl bromides and NH-containingheterocycles is illustrated. Readily available acylhydrazine- and acylhydrazone-typeligands promote the reaction.

Synthesis of indoles via alkylidenation of acyl hydrazides

Indoles have been synthesised via alkylidenation of acyl phenylhydrazides using phosphoranes and the Petasis reagent, followed by in situ thermal rearrangement of the product enehydrazines. The Petasis reagent provides an essentially neutral equivalent of the [acid-catalysed] Fischer indole synthesis, but with acyl phenylhydrazides as starting substrates. Alkylidene triphenylphosphoranes convert aroyl phenylhydrazides to indoles, but acyl phenylhydrazides derived from aliphatic carboxylic acids undergo a Brunner reaction to form indolin-2-ones.

Some Observations on the Brunner Reaction

Elucidation of the stereochemical course of the Brunner reaction is described.A slight modification in the procedure gives better yields and seems very promising for a more general application of this reaction.