132287-04-8

Basic information

• Product Name: 3-(3aH-benzo[d][1,2,3]triazol-1(7aH)-ylamino)cyclohexanone
• Synonyms: 3-(3aH-benzo[d][1,2,3]triazol-1(7aH)-ylamino)cyclohexanone
• CAS NO: 132287-04-8
• Molecular Weight: 215.255
• Mol File: 132287-04-8.mol

Chemical Properties

• CAS DataBase Reference: 3-(3aH-benzo[d][1,2,3]triazol-1(7aH)-ylamino)cyclohexanone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(3aH-benzo[d][1,2,3]triazol-1(7aH)-ylamino)cyclohexanone(132287-04-8)
• EPA Substance Registry System: 3-(3aH-benzo[d][1,2,3]triazol-1(7aH)-ylamino)cyclohexanone(132287-04-8)

Safety Data

• Hazardous Substances Data: 132287-04-8(Hazardous Substances Data)

Upstream product

• 95-14-7 1,2,3-Benzotriazole 
• 930-68-7 cyclohexenone 
• 28539-14-2 N,N-bis(benzotriazol-1-ylmethyl)hydroxylamine 

Relevant articles and documents

Aza-Michael addition of 1,2-diazoles to structurally diverse enones: Efficient methods toward β-amino ketones

An efficient and mild protocol was realized using 1,2-diazoles and related heterocycles with cyclic and acyclic enones in presence of T3P (2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide) toward the regioselective formation of N-cycloalkyl heterocycles at room temperature. The developed reaction conditions showcased good selectivity over a wide range of 1,2-diazoles and enones by delivering N-cycloalkyl heterocycles in excellent yields.

Uncatalysed intermolecular aza-Michael reactions

The catalyst-free reactions of activated alkenes with primary and secondary amines were investigated leading to various mono- and di-hydroamination products, the latter being rare and original. These reactions were shown to depend first on the strength of the nucleophile. Temperature and steric hindrance of the reagents were the other key factors controlling the selectivity of these aza-Michael reactions. In spite of their poor nucleophilicities, some N-heterocyclic amines could react with different activated alkenes affording valuable intermediates. Such results tended to demonstrate the hydrogen-bonding interactions between activated alkenes and poly-nitrogen aromatic cycles may control these concerted or fully conjugate aza-Michael additions.

E-factor minimized protocols for the polystyryl-BEMP catalyzed conjugate additions of various nucleophiles to α,β-unsaturated carbonyl compounds

Efficient protocols for the addition of carbon-, sulphur- and nitrogen-nucleophiles to α,β-unsaturated carbonyl compounds catalyzed by PS-BEMP have been reported. The adoption of solvent-free conditions (SolFC) was crucial for improving the efficiency of all the processes, while by using an organic reaction medium poor results were obtained. Addition reactions were performed by using equimolar amounts of reagents, and the products were isolated by simple filtration with the minimal amount of organic solvent. This approach allowed the E-factor, a measure of the waste of a reaction, to be minimized. Further waste minimization (95.7% compared to batch protocol) has been accomplished by defining a larger scale continuous-flow protocol operating under SolFC.

Intermolecular mono-and dihydroamination of activated alkenes using a recoverable gold catalyst

A combination of gold chloride organometallic complex and a silver salt was used to catalyze intermolecular hydroamination of activated alkenes, i.e aza-Michael reactions. The gold-catalyzed reactions of activated alkenes with nitrogen substrates were investigated and found to afford various mono-and dihydroamination products, the latter being rare and original. After flash chromatography, gold NHC catalyst could be recovered as a gold hydroxide NHC complex. When combined with a silver salt, the gold complex lead again to an active hydroamination catalyst.

Iodine-induced regioselective direct alkylation of azoles via in situ formed alkyliodide

We have developed an efficient, metal-free, convenient and relatively cheap method for iodine-induced direct alkylation of azoles via in situ formed alkyliodide. A series of heterocyclic derivatives are readily prepared under mild conditions in moderate t

Synthesis of β-amino cyclone catalyzed by alkaline Al 2O3

A new method for the synthesis of b-amino cyclone with amines and cyclonene, which was efficiently carried out under solvent free conditions in a short time at room temperature using the catalyst of alkaline Al 2O3 with high yield. T

Organocatalytic enantioselective aza-Michael additions of N-heterocycles to α,β-unsaturated enones

A procedure for enantioselective organocatalytic conjugate additions of a variety of N-heterocycles to α,β-unsaturated enone systems is presented. The reactions are efficiently catalyzed by salts of 9-amino-9-deoxy-epiquinine (3d). Cyclic, acyclic, and aromatic enones can be used in reactions with 1H-benzotriazole (1a) or 5-phenyltetrazole derivatives 12, providing the Michael addition products in high yields and with good to excellent enantioselectivities.

A novel method for the high-pressure-promoted, uncatalyzed aza-Michael reaction of nitrogen heterocycles with enones in water

A new green chemical method for the aza-Michael reaction of nitrogen heterocycles with enones in water as a solvent without the use of any catalysts under high-pressure conditions is described. Georg Thieme Verlag Stuttgart.

THE REACTIONS OF BENZOTRIAZOLE WITH UNSATURATED ALDEHYDES AND KETONES IN THE PRESENCE OR ABSENCE OF AMINES

Benzotriazole adds to α,β-unsaturated aldehydes and ketones with the formation of the corresponding β-benzotriazolyl-aldehydes and -ketones in high yields.Unsaturated aldehydes react with a second molar equivalent of benzotriazole to form 1,3-bisbenzotriazolylalkanols or, in the presence of amines, 1,3-bisbenzotriazolylalkylamines as stable crystalline products.When treated with sodium borohydride or a Grignard reagent, these products undergo substitution of the benzotriazolyl group at C-1 by a hydrogen atom or by an alkyl (or aryl) group, respectively.The 3-benzotriazolylalkylamines obtained were characterized by 1H-NMR and 13C-NMR spectroscopy.Isomerizations between benzotriazol-1-yl and -2-yl derivatives are discussed.

N-Substituted Benzotriazoles as Synthons for 1,3-Dipoles

N-Bis(benzotriazol-1-ylmethyl)hydroxylamine has been shown to be an effective synthon for the nitrone 1,3-dipole.Regio- and stereo-specific cycloaddition with several dipolarophiles to furnish substituted 2-(benzotriazol-1-ylmethyl)isoxazolidines is described.Subsequent replacement of the benzotriazole entity is reported, and reaction of the cycloadducts with perchloric acid is shown to yield isoxazolidines without nitrogen substitution.The synthesis of the novel tricyclic ring system 12-oxa-1,3-diazatricyclo3,8>dodec-5-ene is also reported.Benzotriazol-1-ylmethylene(benzotriazol-1-ylmethyl)amine does not act as a synthon for the azomethine ylide.