Bis(2,2,2-trichloroethyl) Azodicarboxylate

Little, Roger D.; Bregant, Therese M.

doi:10.1002/047084289x.rb198

Cited by 1 publication

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“…It was discovered that fresh and highly purified 31 was required in the preparation of 32. Slightly crude commercial material and the long preparation in Organic Syntheses 21 for 31 prompted us to modify the latter approach. A solution of 1.0 g (0.023 mol) of 85% hydrazine hydrate in 6 mL of 95% ethanol was cooled in an ice bath, and 9.6 g (0.046 mol) of 2,2,2-trichloroethyl chloroformate was added dropwise so that the temperature was kept below 20 °C.…”

Section: 224-tetramethyl-12-dihydroquinoline (27)mentioning

confidence: 99%

“…The reaction mixture was then diluted to 1000 mL with dichloromethane and washed with 5% HCl (2 × 300 mL), saturated sodium bicarbonate (300 mL), water (3 × 300 mL), and saturated NaCl (1 × 300 mL) to give diazo compound 31 as light yellow solid [4.26 g, 56%]: mp 115-116 °C (lit. 21 mp 109-110.5 °C); IR (KBr pellet) 1786, 1723 cm -1 ; 1 H NMR (DCCl3) δ 5.08 (s, 4 H); 13 C NMR (DCCl3) ppm 77.45, 93.09, 158.42. Diazo compound 31 was used immediately to prepare 32.…”

Section: 224-tetramethyl-12-dihydroquinoline (27)mentioning

confidence: 99%

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Novel Heteroarotinoids as Potential Antagonists of Mycobacterium bovis BCG

et al. 2004

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A series of 15 heteroarotinoids has been prepared and evaluated for activity against Mycobacterium bovis BCG with the thiourea-containing isoxyl (7) (0.5 µg/mL) as the standard. 2,2,4-Trimethyl-2H-chromen-7-yl 4-(methoxycarbonyl)benzoate (8) displayed the most significant activity (2.0-4.0 µg/mL) in terms of the lowest concentration (µg/mL) (MIC, minimum inhibitory concentration) required to produce a 99% reduction in the number of colonies on a plate as compared to that system free of the agent at the same dilution of the culture suspension. Ethyl 4-{[N-(2,2,4,4-tetramethylchroman-6-yl)thiocarbamoyl]amino}benzoate (9) and {[(1E,3Z,5E)-1-aza-4-methyl-6-(1,2,2,4-tetramethyl(1,2-dihydroquinolyl))hexa-1,3,5-trienyl]-amino}aminomethane-1-thione (10) exhibited activity at 5.0-10.0 and 10.0-20.0 µg/mL, respectively, while the other examples had MIC values of 20 µg/mL or greater. The inhibitory ability of 8 may occur via the inhibition of mycolic acid synthesis in a like manner as found with 7, but this requires further study. The heteroarotinoids are the first examples to exhibit inhibitory ability against the growth of Mycobacterium bovis BCB.

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Section: 224-tetramethyl-12-dihydroquinoline (27)mentioning

confidence: 99%

Section: 224-tetramethyl-12-dihydroquinoline (27)mentioning

confidence: 99%