The Preparation of Methylthiazoles

Kurkjy, Raymond P.; Brown, Ellis V.

doi:10.1021/ja01142a515

Cited by 40 publications

(22 citation statements)

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“…Six alkyloxazoles and seven alkylthiazoles tentatively identified in the volatiles of freshly roasted Florida Runner peanuts were synthesized by the reaction of corresponding a-bromo ketone with amide (Theilig, 1953) or thioamide (Kurkjy and Brown, 1952). The mass spectral data of synthesized alkyloxazoles and alkylthiazoles are tabulated in Table I.…”

Section: Resultsmentioning

confidence: 99%

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Positive identification of new alkyloxazoles, alkylthiazoles, and piperidine in roasted peanut flavor

Ho¹,

Jin²,

Lee³

et al. 1983

J. Agric. Food Chem.

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Section: Resultsmentioning

confidence: 99%

“…Alkylthiazoles were synthesized by the method of Kurkjy and Brown (1952) by the addition of the cy-bromo ketone to the preformed thioamide. Alkylthiazoles were synthesized by the method of Kurkjy and Brown (1952) by the addition of the cy-bromo ketone to the preformed thioamide.…”

Section: Synthesis Of Alkyloxazolesmentioning

confidence: 99%

Positive identification of new alkyloxazoles, alkylthiazoles, and piperidine in roasted peanut flavor

Ho¹,

Jin²,

Lee³

et al. 1983

J. Agric. Food Chem.

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“…afforded the 2-bromo compound 7 [5] together with the monobromo derivative 2 (ratio 2/7 ϭ 1:4). Carrying out the bromination with NBS in a perfluorinated solvent such as the perfluoro ether FC-77 (C 8 F 16 O, method C) led exclusively to 2-bromo-4,5-dimethylthiazole 7.…”

Section: Resultsmentioning

confidence: 99%

Selective Bromination of 4,5-Dimethylthiazole with N-Bromosuccinimide

et al. 1998

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Radical bromination of 4,5-dimethylthiazole (1) was carried out using different stoichiometries of N-bromosuccinimide in the presence of 2,2Ј-azobisisobutyronitrile. Mono-, tri-and tetrabromo compounds 2, 5, and 6 were obtained in good yields with regioselectivity while the dibromo derivatives 3 and 4 were formed without any selectivity. Substitution at the Polybrominated derivatives of 1,2-dimethylarenes or their heterocyclic analogues are useful precursors for the pro-. The DielsAlder trapping of o-QDMs with dienophiles is an efficient and powerful method for the building of polycyclic aromatic compounds. In order to obtain 5-or 6-functionalized benzothiazoles of biological interest, we planned to prepare selectively the dibromo-, tribromo-or tetrabromomethyl derivatives of 4,5-dimethylthiazole which would further lead to the desired substituted benzothiazole via the corresponding o-QDM (Scheme 1). Scheme 1 Results and DiscussionThe free-radical chlorination of 4-methylthiazole with Nchlorosuccinimide in the presence of benzoyl peroxide or UV radiation has been shown to afford 5-chloro-4-methylthiazole in 95% yield. When chlorination was continued, a decrease of the latter was observed while 5-chloro-4-(chloromethyl)thiazole and 2,5-dichloro-4-(chloromethyl)thiazole were formed in 72 and 24% yield, respectively [4] . The order of reactivity observed was therefore C-5 > 4-Me > C-2.We have performed selective brominations of 4,5-dimethylthiazole (1) with N-bromosuccinimide (NBS). When the commercially available compound 1 was treated with different stoichiometries of NBS in the presence of 2,2Ј-azobisisobutyronitrile (AIBN) under reflux with carbon tetrachloride (method A), the brominated derivatives 2Ϫ6 were selectively obtained (Scheme 2 and Table 1). In contrast, the use of NBS in the presence of silica gel (method B)

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“…The alkylthlazoles were synthesized using the method of Kurkjy and Brown (1952). This involves addition of the cr-bromoketone or cy-bromoaldehyde to the preformed thioamide.…”

Section: Synthesis Of Alkylthiazolesmentioning

confidence: 99%

“…and two alkylthiazoles tentatively identified in the volatiles of cocoa butter from roasted cocoa beans (Carlin, 1980) were synthesized by the reaction of corresponding &bromoketones with amide (Theilig, 1953) or thiomide (Kurkjy and Brown, 1952). The mass spectral data of the synthesized alkyloxazoles and alkylthiazoles are tabulated in Table 1.…”

Section: Seven Alkyloxazolesmentioning

confidence: 99%