2-Aryl-3-acetyl-4(1H)-quinolones<sup>1</sup>

Anderson, Paul C.; Staskun, Benjamin

doi:10.1021/jo01020a034

Cited by 12 publications

(1 citation statement)

References 2 publications

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“…Methyl 3-aminocrotonate 2b, 12 methyl 3-N-methylaminocrotonate 14, 12 ethyl α-(pyrrolidin-2-ylidene)acetate 10, 7 methyl 2-acetamido-3-phenylacrylate 16b, 8 5-p-nitrophenyl-1,2,3-triazole 10 and its 1-p-tolylsulfonyl derivative 18a 10 and methyl 5-methyl-3H-1,2,3-triazole-4-carboxylate (24) 11 were prepared by literature methods. Methyl 3-15 N-aminocrotonate was prepared by treatment of a solution of methyl acetoacetate (900 mg, 7.8 mmol) in water (1 ml) and ethanol (1 ml) with 15 N-enriched ammonia gas which was generated from 15 N-enriched ammonium sulfate (500 mg, 3.9 mmol) (98% enriched) with sodium hydroxide solution.…”

Section: Methodsmentioning

confidence: 99%

Conversion of enamines, enamides and triazoles by trithiazyl trichloride into 1,2,5-thiadiazoles

Rees

Yue

2001

J. Chem. Soc., Perkin Trans. 1

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Trithiazyl trichloride 1 converts primary and secondary enamines, enamides and 1,2,3-triazoles into 1,2,5thiadiazoles. These mild reactions provide one-pot routes to various alkyl, aryl, functional and quaternary 1,2,5-thiadiazoles, in moderate to good yields. The trimer 1 reacts as a 1,2-bis-electrophile adding an N-S unit across C᎐ ᎐ C-N. For primary enamines 15 N-labelling reveals an additional, minor pathway in which N-S-N is added across C᎐ ᎐ C, with elimination of the enamine nitrogen. With N-alkylated enamines the alkyl group is retained in a quaternised thiadiazole, but this can be dealkylated in situ. Enamides react similarly but with spontaneous N-deacylation. 1,2,3-Triazoles with electron withdrawing groups to stabilise their acyclic diazoimine tautomers also give 1,2,5-thiadiazoles, with loss of dinitrogen. Mechanisms are proposed for these new reactions.We have shown that trithiazyl trichloride, (NSCl) 3 , "the trimer" 1 reacts readily with nucleophilic unsaturated substrates, by electrophilic attack or by cycloaddition, to give a useful range of sulfur-nitrogen heterocylic compounds. 1 Thus pyrroles, for example, are converted into isothiazoles or fused 1,2,5thiadiazoles. 2 It seemed that enamines might undergo somewhat analogous reactions, with addition of the trimer across the bisnucleophilic enamine group or across the carbon-carbon double bond, and we now describe these and related reactions. Results and discussion Reactions with primary enaminesWe first treated the stable primary enamines 3-aminocrotononitrile 2a and methyl, ethyl and p-nitrobenzyl 3-aminocrotonates 2b-d with the trimer 1 (1 equiv.

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