132353-25-4

Upstream product

• 3140-73-6 2-chloro-4,6-dimethoxy-1 ,3,5-triazine 
• 100-09-4 4-methoxybenzoic acid 
• 63910-63-4 bis(4,6-dimethoxy-1,3,5-triazin-2-yl) ether 
• 3945-69-5 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride 

Downstream Products

• 36364-17-7 5-(4-methoxyphenyl)-3-phenyl-1,2,4-oxadiazole 
• 39192-94-4 N-(p-methylphenyl)-p-methoxybenzamide 
• 3140-73-6 2-chloro-4,6-dimethoxy-1 ,3,5-triazine 
• 65418-71-5 1,3-bis-(4-methoxyphenyl)-2-ethynyl-1-one 
• 1075-59-8 2-hydroxy-4,6-dimethoxy-1,3,5-triazine 
• 16616-43-6 1-(4-methoxy-phenyl)-3-phenyl-propynone 
• 65418-72-6 1-(4-methoxyphenyl)-3-(4-methylphenyl)-2-ethynyl-1-one 
• 65418-73-7 1-(4-methoxyphenyl)-3-(4-bromophenyl)-2-ethynyl-1-one 
• 93845-81-9 1-(4-methoxyphenyl)hept-2-yn-1-one 
• 603126-31-4 1-(4-methoxyphenyl)-2-nonyn-1-one 
• 93709-64-9 (S)-2-(4-methoxybenzamido) propanoic acid 
• 77876-73-4 2-(4-methoxyphenyl)-4-methyl-5-phenyloxazole 
• 123-11-5 4-methoxy-benzaldehyde 
• 611-94-9 4-Methoxybenzophenone 

Relevant academic research and scientific papers

The design, synthesis, and application of a chiral coupling reagent derived from strychnine for the enantioselective activation of a carboxylic group

The concept of a chiral coupling reagent for the enantioselective synthesis of peptides with a predictable configuration and enantiomeric purity from racemic substrates is presented. The reagent was prepared by treatment of strychninium tetrafluoroborate with 2-chloro-4,6-dimethoxy-1,3,5-triazine in the presence of sodium bicarbonate yielding N-(4,6-dimethoxy-1,3,5-triazin-2-yl)strychninium tetrafluoroborate in high yield, which is stable at room temperature, and in a broad range of solvents gave enriched Z-Ala-Phe-OMe (dr from 95/5 to 60/40) in high yield with d-configuration on the alanine residue starting from rac-Z-Ala-OH.

The effect of counterion and tertiary amine on the efficiency of N-triazinylammonium sulfonates in solution and solid-phase peptide synthesis

A collection of N-triazinylammonium sulfonates, designed according to the concept of "superactive esters", was obtained by treatment of ammonium sulfonates with 2-chloro-4,6-dimethoxy-1,3,5-triazine. The structure of the tertiary amine as well as sulfonate anion influenced their reactivity and stability in N,N-dimethylformamide (DMF) solution. The reagents were successfully used in solution- and solid-phase synthesis of Z-, Boc-, and Fmoc-protected peptides containing natural and unnatural sterically hindered amino acids as well as in [2+1] fragment condensation approaches, yielding the final products in 80-100% yield and high optical purity. In manual SPPS of the [Aib]2[Aib]4-enkephalin analogue and the ACP(65-74) peptide fragment VQAAIDYINEG, several sulfonates yielded peptides significantly faster than TBTU or HATU. Comparative analyses demonstrated that 4-(4,6-di-methoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium 4-toluenesulfonate was the most versatile reagent in a wide range of coupling procedures.

A Strategy for Accessing Aldehydes via Palladium-Catalyzed C?O/C?N Bond Cleavage in the Presence of Hydrosilanes

We report the catalytic reduction of both active esters and amides by selective C(acyl)?X (X=O, N) cleavage to access aldehyde functionality via a palladium-catalyzed strategy. Reactions are promoted by hydrosilanes as reducing reagents with good to excellent yields and with excellent chemoselectivity for C(acyl)?N and C(acyl)?O bond cleavage. Carboxylic acid C(acyl)?O bonds are activated by 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) to form triazine ester intermediates, which further react with hydrosilanes to yield aldehydes in one-pot two-step procedures. We demonstrate that C(acyl)?O cleavage/formylation offers higher yields and broader substrate scopes compared with C(acyl)?N cleavage under the same reaction conditions.

Development of a method for the synthesis of 2,4,5-trisubstituted oxazoles composed of carboxylic acid, amino acid, and boronic acid

A novel method for the synthesis of trisubstituted oxazoles via a one-pot oxazole synthesis/Suzuki–Miyaura coupling sequence has been developed. One-pot formation of 5-(triazinyloxy)oxazoles using carboxylic acids, amino acids and a dehydrative condensing reagent, DMT-MM, followed by Ni-catalyzed Suzuki–Miyaura coupling with boronic acids provided the corresponding 2,4,5-trisubstituted oxazoles in good yields.

One-Pot Synthesis of Arylketones from Aromatic Acids via Palladium-Catalyzed Suzuki Coupling

A palladium-catalyzed one-pot procedure for the synthesis of aryl ketones has been developed. Triazine esters when coupled with aryl boronic acids provided aryl ketones in moderate to excellent yields (up to 95%) in the presence of 1 mol % Pd(PPh3)2Cl2 for 30 min. (Chemical Equation Presented).

Privilege Ynone Synthesis via Palladium-Catalyzed Alkynylation of "Super-Active Esters"

A neat palladium-catalyzed alkynylation reaction was developed with "super-active ester" as the carbonyl electrophile, which provides a clean and efficient synthetic protocol for a broad array of ynone compounds under CO-, Cu-, ligand-, and base-free conditions. The superior activity of triazine ester was rationalized by the strong electron-withdrawing ability and the unique affinity of triazine on palladium. A mechanistic experiment clearly demonstrated that the N-Pd coordination of triazine plays a crucial role for the highly efficient C-O activation. (Chemical Equation presented).

Synthesis of chiral triazine coupling reagents based on esters of n-alkylproline and their application in the enantioselective incorporation of d or l amino acid residue directly from racemic substrate

Esters of N-methylproline and N-allylproline were prepared and used as component for synthesis of chiral triazine based coupling reagents. N-Triazinylammonium tetrafluoroborate obtained from methylester of L-N-methylproline, 2-chloro-4,6-dimethozxy-1,3,5-

P-Triazinylphosphonium chlorides as a new group of coupling reagents

Tertiary phosphines in reaction with 2-chloro-4,6-dialkoxy-1,3,5-triazines gave unstable quaternary P-triazinylphosphonium chlorides, which readily decomposed with a departure of the alkyl group of the triazine ring substituent. Stable quaternary P-triazinylphosphonium chlorides were obtained only in reaction of 2-chloro-4,6-diphenoxy-1,3,5-triazine. Both, stable quaternary P-triazinylphosphonium chlorides as well unstable analogues prepared in situ activated carboxylic acid yielding "superactive" triazine esters, useful as highly efficient reagents in peptide bond synthesis.

A simple and straightforward protocol to 3,5-disubstituted 1,2,4-oxadiazoles from carboxylic acids

A convenient one-pot synthesis of 1,2,4-oxadiazoles is described. The condensation of carboxylic acids and amidoximes in the presence of 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) and N-methylmorpholine (NM1 B) has been employed to synthesize a variety of 3,5-disubstituted 1,2,4-oxadiazoles in good to excellent yields. The methodology has been applied for the synthesis of a metabotropic glutamate subtype 5 (mGlu5) receptor antagonist.

Bis(4,6-dimethoxy-1,3,5-triazin-2-yl) ether as coupling reagent for peptide synthesis

Bis(4,6-dimethoxy-1,3,5-triazin-2-yl) ether (4) was prepared by treatment of 2-hydroxy-4,6-dimethoxy-1,3,5-triazine with 2-chloro-4,6-dimethoxy-1,3,5- triazine in 61% yield. Ether 4, isoelectronic with pyrocarbonates, was found capable to activate carboxylic acids in the presence of 1,4-diazabicyclo[2.2.2] octane (DABCO) to yield, under mild reaction conditions, superactive triazine esters. Versatility of this new coupling reagent was confirmed by condensation of lipophilic and sterically hindered carboxylic acids with amines in 71-98% yield, and by synthesis of peptides, including those containing Aib-Aib sequence, in solution with high yield and high enantiomeric purity. Copyright