- Characteristic flavor formation of thermally processed N-(1-deoxy-α-D-ribulos-1-yl)-glycine: Decisive role of additional amino acids and promotional effect of glyoxal
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The role of amino acids and α-dicarbonyls in the flavor formation of Amadori rearrangement product (ARP) during thermal processing was investigated. Comparisons of the volatile compounds and their concentrations when N-(1-deoxy-α-D-ribulos-1-yl)-glycine r
- Zhan, Huan,Cui, Heping,Yu, Junhe,Hayat, Khizar,Wu, Xian,Zhang, Xiaoming,Ho, Chi-Tang
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- Carbonylative Acetylation of Heterocycles
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Herein, a new procedure for the carbonylative acetylation of heterocycles has been developed. In this process, organic peroxide acts as the methyl source. Various heterocycles were transformed into the corresponding methyl heterocyclic ketones in moderate to good yields.
- Zhang, Youcan,Yin, Zhiping,Wu, Xiao-Feng
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supporting information
p. 213 - 216
(2020/01/22)
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- Synthetic method for 2-acetyl thiazole
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The invention relates to a synthetic method for 2-acetyl thiazole. The synthetic method comprises the following steps: firstly, preparation of 2-amino thiazole is carried out, namely, toluene, thiourea and chloroacetaldehyde are mixed, a reaction is carried out with stirring at a constant temperature, and 2-amino thiazole is prepared; secondly, preparation of 2-bromo thiazole is carried out, namely, 2-amino thiazole is dissolved in sulfuric acid, cooling is carried out, a sodium nitrite aqueous solution is added drop by drop slowly at a controlled temperature after concentrated nitric acid is added drop by drop, stirring is carried out continuously, a reaction is carried out, the solution after the reaction is added in a mixed solution of sodium bromide and copper sulphate, a bromination reaction is carried out, and 2-bromo thiazole is prepared; thirdly, preparation of 2-acetyl thiazole is carried out, namely, 2-bromo thiazole is added in a butyllithium solution, stirring is carried out, then ethyl acetate is added, a reaction is carried out, and 2-acetyl thiazole is prepared. The acetylation step of 2-bromo thiazole is improved, the reaction raw material ratio and the reaction temperature are optimized, the high yield of the reaction is achieved, safe and reliable operation of the experiment is ensured effectively, and unexpected technical effects are achieved.
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Paragraph 0050; 0051
(2016/10/08)
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- Mechanism of formation of sulphur aroma compounds from l-ascorbic acid and l-cysteine during the Maillard reaction
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The sulphur aroma compounds produced from a phosphate-buffered solution (pH 8) of l-cysteine and l-, l-[1-13C] or l-[4-13C] ascorbic acid, heated at 140 ± 2 °C for 2 h, were examined by headspace SPME in combination with GC-MS. MS data indicated that C-1 of l-ascorbic acid was not involved in the formation of sulphur aroma compounds. The sulphur aroma compounds formed by reaction of l-ascorbic acid with l-cysteine mainly contained thiophenes, thiazoles and sulphur-containing alicyclic compounds. Among these compounds, 1-butanethiol, diethyl disulphide, 5-ethyl-2-methylthiazole, cis and trans-3,5-dimethyl-1,2,4-trithiolane, thieno[2,3-b]thiophene, thieno[3,2-b]thiophene, cis and trans-3,5-diethyl-1,2,4-trithiolane, 1,2,5,6-tetrathiocane, 2-ethylthieno[2,3-b]thiophene, 2,4,6-trimethyl-1,3,5- trithiane and cyclic octaatomic sulphur (S8) were formed solely by l-cysteine degradation, and the rest by reaction of l-ascorbic acid degradation products, such as hydroxybutanedione, butanedione, acetaldehyde, acetol, pyruvaldehyde and formaldehyde with l-cysteine or its degradation products, such as H2S and NH3. A new reaction pathway from l-ascorbic acid via its degradation products was proposed.
- Yu, Ai-Nong,Tan, Zhi-Wei,Wang, Fa-Song
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experimental part
p. 1316 - 1323
(2012/06/30)
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- Aroma compounds generated from thermal reaction of l-ascorbic acid with l-cysteine
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The reaction of l-ascorbic acid with l-cysteine in heated aqueous solution (141 ± 1 °C) at five different pH values (5.00, 6.00, 7.00, 8.00, or 9.00) for 2 h, resulted in the formation of a complex mixture of aroma volatiles. The volatile compounds generated were analysed by SPME-GC-MS. The results gave 43 aroma compounds. The reaction between l-ascorbic acid and l-cysteine led mainly to the formation of alicyclic sulphur compounds, thiophenes, thienothiophenes, thiophenones, thiazoles and pyrazines, most of which contain sulphur. Many of these volatiles had meaty flavour. The origin of many of the compounds was explained. The studies showed that thienothiophenes and thienones were formed mainly at acidic pH. In contrast, higher pH values could promote the production of thiophenes, thiazoles and pyrazines.
- Yu, Ai-Nong,Zhang, Ai-Dong
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experimental part
p. 1060 - 1065
(2011/12/02)
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- Discovery and SAR of novel 4-thiazolyl-2-phenylaminopyrimidines as potent inhibitors of spleen tyrosine kinase (SYK)
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A series of SYK inhibitors based on the phenylamino pyrimidine thiazole lead 4 were prepared and evaluated for biological activity. Lead optimization provided compounds with nanomolar Ki's against SYK and potent inhibition in mast cell degranulation assays.
- Farmer, Luc J.,Bemis, Guy,Britt, Shawn D.,Cochran, John,Connors, Martin,Harrington, Edmund M.,Hoock, Thomas,Markland, William,Nanthakumar, Suganthini,Taslimi, Paul,Haar, Ernst Ter,Wang, Jian,Zhaveri, Darshana,Salituro, Francesco G.
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scheme or table
p. 6231 - 6235
(2009/08/07)
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- THIAZOLES USEFUL AS INHIBITORS OF PROTEIN KINASES
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The present invention relates to compounds useful of inhibitors of protein kinases. The invention also provides pharmaceutically acceptable compositions comprising said compounds and methods of using the compositions in the treatment of various disease, conditions, or disorders.
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- Thiazole, imidazole and oxazole compounds and treatments of disorders associated with protein aging
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Provided are, among other things, compounds of formula I or IA, . Also provided are methods of treatment with such compounds.
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- Method for treating glaucoma IIB
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Provided is a method of decreasing intraocular pressure or improving ocular accommodation in an animal, including a human, comprising administering an intraocular pressure decreasing amount or ocular accommodation improving amount of a compound of the formula I or IA, wherein J is oxygen, sulfur, or N—Rd.
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- Efficient electron-donating groups for nonlinear optical applictions
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Nonlinear optical materials having structures with delocalized resonance configurations corresponding to: or: wherein A is a first electron accepting group, R is pi-conjugated non-centrosymmetric organic moiety; R4 and R5 are independently selected from hydrogen, alkyl moieties and functionalized alkyl moieties; E, F, G and H are members of a saturated or unsaturated five- to ten-membered cyclic ring or two-ring systems having five- to ten-membered rings that are electron donating in nature and E, F, G and H are independently selected from -CH-, -CH2-, O, S, N, Se, Te, and -NR2-, wherein R2 is selected from hydrogen, alkyl moieties and functionalized alkyl moieties; and R1 is selected from alkyl moieties and functionalized alkyl moieties. Polymers blended with or having the disclosed nonlinear optical materials as pendant side chains and exhibiting second order nonlinear optical properties are also disclosed.
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- Kinetic Resolution of 1-Aryl- and 1-Heteroaryl Ethanols by Oxidation with Baker's Yeast
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The kinetic resolution of racemic 1-aryl and 1-heteroaryl ethanols 1a-e via oxidation by Baker's yeast to give the R-enantiomer is reported.Key Words: Kinetic resolution, Oxidation, Baker's yeast, 1-Aryl ethanol, 1-Heteroaryl ethanol
- Fantin, Giancarlo,Fogagnolo, Marco,Medici, Alessandro,Pedrini, Paola,Poli, Silvia,Sinigaglia, Milena
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p. 883 - 884
(2007/10/02)
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- 1,2,3-TRIAZOLOTHIAZOLES; SYNTHESIS AND PROPERTIES
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The synthesis of 1,2,3-triazolothiazole (15) and its 3-methyl- (16) and 3-phenyl- (17) derivatives is reported, together with their spectra, quaternisation, and ring opening reactions.
- Jones, Gurnos,Ollivierre, Hermione,Fuller, L. S.,Young, J. H.
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p. 2851 - 2860
(2007/10/02)
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- 2-ACETHYLTHIAZOLE AS ATHREE-CARBON HOMOLOGATING REAGENT OF ALDEHYDES. APPLICATION TOWARD THE SYNTHESIS OF AMINO HEXOSES FROM L-SERINAL
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2-Acetylthiazole (1) serves as asource of the α-hydroxypropanal β-anion synthon for the conversion of aldehydes into syn and anti α,γ-dihydroxy homologues with three-more carbon atoms via a sequence consisting of:i) aldol condensation of the lithium enolate derived from 1; ii) reduction of the hydroxy ketone; iii) thiazole to formyl unmasking.The methodology is employed for the conversion of L-serinal into amino sugars.
- Dondoni, Alessandro,Fantin, Giancarlo,Fogagnolo, Marco
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p. 6063 - 6066
(2007/10/02)
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- Synthesis of (Trimethylsilyl)thiazoles and Reactions with Carbonyl Compounds. Selectivity Aspects and Synthetic Utility
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Synthetic routes to all possible regioisomeric mono- and bis(trimethylsilyl)thiazoles as well as to the tris(trimethylsilyl) derivative via lithiation-silylation sequences of the thiazole ring followed by selective protodesilylation in some cases are described. (Trimethylsilyl)thiazoles serve as thiazolyl donor synthons upon reaction with carbonyl compounds (ketenes, acyl chlorides, aldehydes) for the preparation of mono- and bis-substituted thiazoles in very good yields.Carbodesilylation occurs more readily at the 2- than 5-position, whereas no reaction takes place at the 4-position.A mechanism via a thiazolium 2-ylide as an intermediate is suggested for the carbodesilylation at the 2-position.
- Dondoni, Alessandro,Fantin, Giancarlo,Fogagnolo, Marco,Medici, Alessandro,Pedrini, Paola
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p. 1748 - 1761
(2007/10/02)
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- MICROBIOLOGICAL SYNTHESIS OF VARIOUSLY PROTECTED L-GLYCERALDEHYDES IN HIGH OPTICAL PURITY
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Variously protected L-glyceraldehydes have been enantioselectively synthesized through a sequence involving acylation of formylanion equivalents with glycolic acid derivatives followed by baker's yeast mediated reduction of the resulting ketones.
- Guanti, Giuseppe,Banfi, Luca,Narisano, Enrica
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p. 3547 - 3550
(2007/10/02)
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- NEW PERSPECTIVES IN THIAZOLE CHEMISTRY
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Carbon-carbon bond forming reactions at C-2 of the thiazole ring have been carried using two strategies, one involving the addition of organometallic reagents (lithium carbanions of esters, Grignard salts, silyl enol ethers, silyl ketene acetals, silylazoles) to N-acylthiazolium salts; the other involving the addition of carbon electrophiles (ketenes, acyl chlorides, anhydrides, aldehydes) to N-acylthiazolium ylides generated in situ.The reactions have been applied to 1,3-thiazole and 2-trimethylsilyl-1,3-thiazole, the latter being more reactive than the former toward electrophiles.This methodology constitutes a new entry to a variety of functionalized thiazoles and thiazolines which are potential building blocks for the synthesis of natural compounds and analogues of biologically active molecules (penems, arylpropionic acids).Some ring transformations of thiazoles induced by carbon-sulfur bond cleavage are also described.The fundamental role played by the sulfur atom of the thiazole ring in the observed reactions is pointed out and briefly discussed.
- Dondoni, Alessandro
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- Additions and Cycloadditions of Ketenes to 1,3-Thiazole and Its Alkyl Derivatives
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1,3-Thiazole and its 4-methyl and 5-methyl derivatives react with tert-butylcyanoketene (TBCK) and dichloroketene (DCK), affording Michael-type addition products at C2, viz., 2-acylthiazoles, and 2:1 cycloadducts (with TBCK only) which proved by X-ray analysis to be bicyclic systems constituted by a thiazoline and a piperidine-1,3-dione ring condensed across the C-N bond. 2-Ethyl- and 2-isopropyl-1,3-thiazole undergo acylation by DCK at the Cα of the alkyl chain.The latter thiazole gives also a 2:1 cycloadduct, which X-ray analysis showed to be a bicyclic system constituted by a thiazoline and an oxazinone ring condensed across the C-N bond.A mechanism is envisaged involving the quaternization of the thiazole nitrogen by the ketene to give an N-thiazolium enolate system which owing to proton exchange between the C2 of the ring or the Cα of the 2-alkyl chain and its enolate portion is in equilibrium with an N-acylthiazolium ylide or zwitterion, respectively.Subsequent reactions of these active intermediates with the ketene lead to the final products.
- Medici, Alessandro,Fantin, Giancarlo,Fogagnolo, Marco,Pedrini, Paola,Dondoni, Alessandro,Andreetti, Giovanni Dario
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p. 590 - 596
(2007/10/02)
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- REACTIONS OF 2-TRIMETHYLSILYLYHIAZOLE WITH ACYL CHLORIDES AND ALDEHYDES SYNTHESIS OF NEW THIAZOL-2-YL DERIVATES
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2-Trimethylsilylthiazole (1) undergoes ipso-substitution of the silyl group with various acyl chlorides and ethyl chloroformate affording 2-acylthiazoles (2)-(5) but adds by the carbon-silicon bond to the carbonyl group of aldehydes yielding thiazol-2-yl-trimethylsiloxy-methane derivates (7).
- Medici, Alessandro,Fantin, Giancarlo,Fogagnolo, Marco,Dondini, Alessandro
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p. 2901 - 2904
(2007/10/02)
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- 2-Alkoxy(and 2-alkoxyalkyl)-2-heterocyclic-thioacetamides for inhibiting gastric acid secretion
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The compounds are 2-alkoxy(and 2-alkoxyalkyl)-2-heterocyclic-thioacetamides which are inhibitors of gastric acid secretion.
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