20353-93-9

Usage

Uses

Used in Pharmaceutical Industry:
(DIMETHYLAMINOMETHYLENE-AMINOMETHYLENE)DIMETHYLAMMONIUM CHLORIDE is used as an intermediate compound for the synthesis of various pharmaceuticals. Its cationic nature allows it to interact with biological targets, making it a valuable component in the development of new drugs.
Used in Chemical Synthesis:
In the field of chemical synthesis, (DIMETHYLAMINOMETHYLENE-AMINOMETHYLENE)DIMETHYLAMMONIUM CHLORIDE serves as a key building block for the creation of more complex molecules. Its reactivity and structural features enable the formation of a wide range of compounds with diverse applications.
Used in Gold's Reagent Synthesis:
(DIMETHYLAMINOMETHYLENE-AMINOMETHYLENE)DIMETHYLAMMONIUM CHLORIDE is used as a component in the synthesis of Gold's Reagent, which is then utilized in the preparation of 4-hydroxyquinazoline by reacting with ortho aminobenzoic acids. This application highlights its importance in the development of synthetic methods and the production of various chemical compounds.

Upstream product

• 68-12-2 N,N-dimethyl-formamide 
• 108-77-0 1,3,5-trichloro-2,4,6-triazine 

Downstream Products

• 20973-68-6 1-dimethylamino-2-p-nitrophenyl-ethylene 
• 52200-09-6 2-benzoyl-3-(dimethylamino)-2-propenenitrile 
• 77022-33-4 3,5-dicyano-4-(N,N-dimethylformamidino)-2,6-diphenyl-4H-pyran 
• 136709-53-0 ethyl 1-benzyl-4-(1,2,4-triazol-1-yl)piperidine-4-carboxylate 
• 924-99-2 ethyl 3-(dimethylamino)acrylate 
• 16849-87-9 2-(4b-dimethylaminomethylene)-2-cyano ethyl acetate 
• 32084-59-6 6-bromoquinazolin-4(3H)-one 
• 18856-68-3 diethyl N,N-dimethylaminomethylenemalonate 
• 273928-10-2 N,N-Dimethyl-N'-(dimethylaminomethyl)formamidinium-chlorid 
• 179688-01-8 7-benzyloxy-6-methoxy-3,4-dihydroquinazolin-4-one 
• 1056056-19-9 3-[2-(2-fluoro-4-methoxy-phenyl)-ethyl]-7-nitro-3H-quinazolin-4-one 
• 1898-74-4 2,4-diphenyl-1,3,5-triazine 
• 71565-88-3 N,N-(dimethylaminomethylene)-3-pyridinecarboxamide 
• 121876-96-8 4-Dimethylamino-2-phenyl-1-oxa-3-azabuta-1,3-diene 

Relevant academic research and scientific papers

Facile synthesis and in-vitro antitumor activity of some pyrazolo[3,4-b]pyridines and pyrazolo[1,5-a]pyrimidines linked to a thiazolo[3,2-a]benzimidazole moiety

The key precursor E-3-(N,N-dimethylamino)-1-(3-methylthiazolo[3,2-a] benzimidazol-2-yl)prop-2-en-1-one 4 was synthesized in good yield using Gold's reagent. The reaction of enaminone 4 with 5-amino-3-aryl-1-phenylpyrazoles 5a, b in refluxing acetic acid in the presence of sulphuric acid, yielded pyrazolo[3,4-b]pyridines 7a, b. Similarly, pyrazolo[1,5-a]pyrimidines 10a, b and 14a-f were prepared by reaction of enaminone 4 with 5-amino-1H-pyrazoles 8a, b and 12a-f, respectively. The structure of pyrazolo[1,5-a]pyrimidine 10b was determined by X-ray diffraction. The synthesized compounds were tested for their in-vitro antitumor activity against the colon cancer cell line CaCo-2; their cytotoxicity against the normal fibroblast cell line BHK was explored as well. Some of the tested compounds exhibited cell growth inhibitory activity. The significant antitumor activity of compound 14f against the CaCo-2 cell line (IC50 = 0.5 μg/mL) was coupled with a lower toxicity against BHK (IC50 = 2.3 μg/mL).

Scalable synthesis of enaminones utilizing Gold's reagents

Several Gold's reagents were synthesized from cyanuric chloride and N,N-dialkylformamides. These synthetic equivalents of N,N-dimethylformamide dimethyl acetal were used in an optimized and scalable procedure for the regioselective synthesis of a variety

One-pot synthesis of enaminones using gold's reagent

Enaminones were efficiently prepared via modification for Gupton method, which depends on carrying out the latter procedure in one step reaction, avoiding the isolation of [3-(dimethylamino)-2-azaprop-2-en-1-ylidene] dimethylammonium chloride (Gold's reag

Method for producing dicarbonyl compounds

The invention relates to a method for producing α-dicarbonyl compounds of formula (I), wherein R1 and R2, independently of each other, mean C1-6-alkyl. Said method is characterised in that an α,β-unsaturated ketone of formula (II), wherein R1 and R2 have the meaning above and R3 and R4, independently of each other, mean hydrogen, C1-6-alkyl or di-C1-6-alkylamino, is reacted with ozone and the resulting ozonide is treated reductively.

Orthoamides. LIV. Contributions to the chemistry of azavinylogous orthoformic acid amide derivatives

The azavinylogous aminalester 3 reacts with primary amines to give amidines 5 and 6. In the reaction of 3 with aniline the azavinylogous amidine 7 is produced additionally to the amidine 5c. Ethylendiamine is formylated at both aminogroups, the bis-amidine 8 thus formed is transformed to the salts 9a,b. Benzoxazole and benzimidazole can be prepared from 3 and o-aminophenol and o-phenylenediamine, resp. Carboxylic acid amides, urea, thiourea, aromatic acid hydrazides 17 and the sulfonylhydrazide 19 are formylated by 3 at nitrogen to give N-acylated formamidines 14, 16, 18, 20. From 3 and aliphatic acid hydrazides 17 and alkylhydrazines, resp., can be obtained 1,2,4-triazole 21 and 1-alkyl-1,2,4-triazoles 22a,b, resp. N.N-Dimethylcyanacetamide (32) reacts with 3 and the orthoamide 4a, resp., to give a mixture of the formylated compound 34 and the amidine 33. The reaction conditions are of low influence on the ratio in which 33 and 34 are formed. The orthoamide 4b and 32 react to afford a mixture of the amidine 35 and the enamine 36. Hydrogen-sulfide acts on 3 giving N,N-dimethylthioformamide (37). From 3 and 1-alkynes 41 can be prepared the amidines 42. Hydrolysis of 42b affords phenylpropiolaldehyde (43). The alkylation of the aminalester 3 gives rise to the formation of vinylogous amidinium salts 1c and 1d, resp., additionally is formed the amide acetal 2a. The salt 1d can also be prepared from 3 and borontrifluoride-ether. Iodide reacts with N,N-dimethylformamide acetals 12a,b in an unclear, complicated manner giving orthoesters 53, N,N-dimethylformamide, alkyliodides, alcohols, ammonium iodides 46 and carbondioxide. The action of halogens on 3 affords the salts 1a,b,c,e,f depending on the chosen stoichiometric ratio. Aromatic aldehydes are suited for trapping azavinylogous carbenes formed on thermolysis of 3; 1,3-oxazoles 69 are the reaction products. From 3 and propionaldehyde the amidine 65 can be obtained with low yield. Carbondisulfide transforms 3 to the azavinylogous salt 66. The preparation of the azavinylogous orthoamide 4a is described. The thermolysis of 3 and 4a, resp., gives rise to the formation of the triaminopyrimidine 67. Treatment of 1a with lithium diisopropylamide affords the triaminopyrazine 68, which can also be obtained by thermolysis of 3 in the presence of sodium hydride. Azavinylogous carbenes are thought to be the intermediates. Wiley-VCH Verlag GmbH, 2000.

Process for preparing substituted pyrimidine derivatives

PCT No. PCT/EP98/00074 Sec. 371 Date Dec. 17, 1999 Sec. 102(e) Date Dec. 17, 1999 PCT Filed Jan. 8, 1998 PCT Pub. No. WO98/30549 PCT Pub. Date Jul. 16, 1998A process for preparing substituted pyrimidine derivatives of the general formula (I): in which a [3-(dimethylamino)-2-azaprop-2-en-1-ylidine]dimethylammonium halide is reacted with a substituted acetamide. The compounds of general formula (I) are important intermediate products for pharmaceutical or agrochemical active substances.

New synthesis of 1,5-disubstituted imidazoles

A new synthesis of 1-alkylimidazole-5-carbaldehydes starting from [3- (dimethylamino)-2-azaprop-2-enylidene]dimethylammonium chloride and alkyl N- alkylglycinate is described.