24294-83-5

Upstream product

• 692256-83-0 1-amino-3-methyl-butan-2-one 
• 97-94-9 triethyl borane 
• 74152-17-3 3-chloro-2,5-bis(1-methylethyl)pyrazine 
• 870544-21-1 1-azido-3-methylpentan-2-one 
• 76779-97-0 1-azido-3-methylbutan-2-one 
• 870544-28-8 1-azido-4-methylpentan-2-one 
• 16369-05-4 valinol 
• 75-26-3 isopropyl bromide 
• 29460-90-0 2-(1-methylethyl)pyrazine 
• 67-64-1 acetone 
• 557-20-0 diethylzinc 
• 6216-65-5 N-benzyloxycarbonyl-L-valinol 
• 4070-48-8 L-valine methyl ester 
• 138754-84-4 N-benzyloxycarbonyl-L-valinal 

Downstream Products

• 154559-11-2 2,5-diisopropylpiperazine 
• 114362-37-7 (+/-)-cis-1,4-dibenzyl-2,5-diisopropylpiperazine 
• 114362-38-8 trans-1,4-dibenzyl-2,5-diisopropylpiperazine 

Relevant academic research and scientific papers

Discovery of (Dihydro)pyrazine N-Oxides via Genome Mining in Pseudomonas

Overexpression of the Pseudomonas virulence factor (pvf) biosynthetic operon led to the identification of a family of pyrazine N-oxides (PNOs), including a novel dihydropyrazine N,N′-dioxide (dPNO) metabolite. The nonribosomal peptide synthetase responsib

Synthesis of Pyrazines and Quinoxalines via Acceptorless Dehydrogenative Coupling Routes Catalyzed by Manganese Pincer Complexes

Base-metal catalyzed dehydrogenative self-coupling of 2-amino alcohols to selectively form functionalized 2,5-substituted pyrazine derivatives is presented. Also, 2-substituted quinoxaline derivatives are synthesized by dehydrogenative coupling of 1,2-diaminobenzene and 1,2-diols. In both cases, water and hydrogen gas are formed as the sole byproducts. The reactions are catalyzed by acridine-based pincer complexes of earth-abundant manganese.

A new method for the synthesis of symmetrical disubstituted pyrazines

Through the self-condensation of α-amino aldehydes, the synthesis of symmetrical disubstituted pyrazines was achieved in a three-step one-pot reaction. The α-amino aldehydes were easily obtained by treating methyl esters of natural α-amino acids with diisobutylaluminium hydride.

Pyrazine alkaloids via dimerization of amino acid-derived α-amino aldehydes: Biomimetic synthesis of 2,5-diisopropylpyrazine, 2,5-bis(3- indolylmethyl)pyrazine and actinopolymorphol C

The dimerization of amino acid-derived α-amino aldehydes provides a short, biomimetic synthesis of several 2,5-disubstituted pyrazine natural products. The α-amino aldehyde intermediates were generated in situ by the hydrogenolysis of their Cbz-derivative

Synthesis of peptides and pyrazines from β-amino alcohols through extrusion of h2 catalyzed by ruthenium pincer complexes: Ligand-controlled selectivity

Your choice: The choice of the Ru-pincer-complex catalyst determines if peptides or pyrazines are formed from β-amino alcohols. Use of PNN complex 1 leads to linear poly(alanine) or to cyclic dipeptides, depending on the R group (see scheme). With the PNP

Novel pyrazines from the myxobacterium Chondromyces crocatus and marine bacteria

The volatiles released by two strains of the myxobacterium Chondromyces crocatus and seven strains of marine Alpha-proteobacteria from the North Sea were collected using the CLSA or SPME headspace methods and analysed by GC-MS. In the extracts of C. crocatus 27 pyrazines were identified, belonging to different classes. 2,5-Dialkylpyrazines and related 3-methoxy-2,5- dialkylpyrazines dominated. Several pyrazines like 2-(1-methylethenyl)-5-(1- methylethyl)-pyrazine (7) and 3-methoxy-2,5-dialkylpyrazines with methyl, isopropyl, isobutyl or sec-butyl side-chains were obtained from natural sources for the first time. It was essential for the identification to rely on synthetic reference materials, which were obtained using Fuerstner's iron-catalysed coupling of chloropyrazines with Grignard reagents or condensation of azido ketones as key steps. The synthetic material allowed the identification of two previously unknown attractants of bacterial origin for the pineapple beetle Carpophilus humeralis, namely 3-methoxy-2-(1-methylpropyl)-5-(2-methylpropyl) pyrazine (17) and 3-methoxy-2,5-bis(1-methylpropyl)pyrazine (52). Several 2,5-dialkylpyrazines were identified in the extracts of the marine Alphaproteobacteria. The unique 2,5-dimethyl-3-(methylsulfanyl)pyrazine (67) represents a new type of natural pyrazine. Our results, together with literature reports, show that pyrazines are an important class of bacterial volatiles which might be more widespread than previously thought. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

Identification and synthesis of volatiles released by the myxobacterium Chondromyces crocatus

Cultures of the myxobacterium Chondromyces crocatus on agar plates were analysed by closed-loop-stripping analysis or solid phase micro extraction. The odour profiles consist mainly of pyrazines, sesquiterpenoids and some aromatic compounds, summing up to more than 50 components. Several new pyrazines as 2-(1-hydroxy-1-methylethyl)-3-methoxypyrazine (9), 2-(1-hydroxy-1-methylpropyl)- 3-methoxypyrazine (10), and 2-(1-hydroxy-2-methylpropyl)-3-methoxypyrazine (11) were identified besides several known pyrazines. A major pyrazine occurring in most samples was 2,5-bis-(1-methylethyl)pyrazine (3). While the well known sesquiterpenoid geosmin (1) was present in low amounts, the related compound (1(10)E,5E)-germacradien-11-ol (21) was identified in most samples in larger quantities. Other prominent sesquiterpenoids not reported before from microorganisms were (6S,10S)-6,10-dimethylbicyclo[4.4.0]dec-1-en-3-one (16), which was accompanied by smaller amounts of several derivatives. The biosynthesis of these compounds is discussed in relation to the recently proposed biosynthetic pathways to 1 and 21.

Identification of host-related volatiles attractive to pineapple beetle Carpophilus humeralis

Volatiles collected from oranges fed upon by Carpophilus humeralis of either sex were consistently more attractive than volatiles from beetle-free oranges in wind-tunnel bioassays. Three compounds were identified as attractants from this system: 4-ethyl-2-methoxyphenol (1), 2,5- diisopropylpyrazine (2) (a new natural product), and 2-phenylethanol (3). Identifications were confirmed with synthetic compounds that had matching chromatographic and spectral properties. Compounds 1, 2, and 3 had only slight activity alone, but were highly synergistic with each other and with propyl acetate (PA), a fruity ester that is mildly attractive to Carpophilus beetles. Compound 2 was the most active in the wind tunnel; its threshold dose was 0.5 ng when PA was present. The structural specificity for these compounds was high. Twelve phenol analogs of 1 were tested, but only one of these, 2-methoxyphenol, was more attractive than the control. Similarly, the analogs of 2, 2-isopropylpyrazine and 2,6-diisopropylpyrazine, were completely inactive. In the field, a combination of 1, 2, and 3 was not attractive by itself, but it strongly synergized attraction to fermentation volatiles, Carpophilus pheromones, or both. Compounds 1, 2, and 3 apparently have a microbial origin because all three were detected when the host fruit was pineapples instead of oranges, because they could occur in the absence of beetles, and because autoclaved pineapple began to produce the compounds after inoculation from an attractive piece of fruit. The study demonstrated that host location for this generalist species can be far more complex than responding simply to the bouquet of low-molecular-weight volatiles normally associated with fermentation.

ETHYLATION OF PYRAZINES USING ALKYLMETALS, SUCH AS TRIETHYLALUMINUM, DIETHYLZINC, AND TRIETHYLBORANE

Triethylaluminum, diethylzinc and triethylborane were used for the ethylation of pyrazines.Among these reagents, triethylborane gave the best results.