Thio benzamide

A convenient route to 2-alkylthio-4-alkyl-4-hydroxy-5,6-dihydro-4/7-l,3-thiazine derivatives 176 is the reaction of A-alkyldithiocarbamates with a,/3-unsaturated ketones in the presence of boron trifluoride etherate at 0°C (Scheme 15) <2002HAC377>. The predominant diastereomer displayed a m-relationship between the hydroxyl group and the C-4 substituent. Subsequent dehydration led to two isomeric products 177 and 178 with an equilibrium mixture resulting in a ratio of 94 6 in the case of 2-benzylthio-4-hydroxy-4-methyl-5,6-dihydro-4/7-l,3-thiazine. 2-Phenyl-4-alkyl-4-hydroxy-5,6-dihydro-4/7-l,3-thiazine derivatives are similarly prepared by reacting thio-benzamide with o ,/3-unsaturated ketones at room temperature <2002EJP307>. 

Sakamoto et al. provided an example of absolute asymmetric synthesis involving hydrogen abstraction by thiocarbonyl sulfur (Scheme 6). [24] Achiral A -diphenylacetyl-iV-isopropylthiobenzamide 33 and Y-diphenylacetyl-A-isopropyl(p-chloro)thio-benzamide 33 crystallize in chiral space group P2 2 2. Photolysis of the chiral crystals in the solid state gave optically active azetidin-2-ones whereas achiral thioketones were obtained as main products. When 33a was irradiated in the solid state at -45°C followed by acetylation (at -78°C), 2-acetylthio-3,3-dimethyl-l-diphenylacetyl-2-phenylaziridine (34a 39% yield, 84% ee), 4-acetylthio-5,5-dimethyl-2-diphenylmetyl-4-phenyloxazoline (35a 10% yield, 50% ee), 3,3-diphenyl-1-isopropy 1-4-... 

Ach, D. Reboul, V. Metzner, P. Atroposelec-tivity of reactions of benzylic metalated thio-benzamides and thionaphthamides. Ear. J. 

BenZoylamino-thiocarbonyl)-ethoxycarbonyl-methyll-4-hydroxy- 8 2-Benzoyl-3-benzyl-5-ethoxycarbonyl-4-methyl-2,3-dihydro- 356 5-Benzoyl-2,4-bis-[4-methoxy-phcnyl]-aus 4-Methoxy-N-(4-methoxy-a-morpholino-bcnzyliden)-thio-benzamid und -Brom-aceto-phcnon 135 5-Benzoyl-2-chlor- 263... 

Huisgen and his co-workers allowed thiobenzophenone to react with the meso-ionic compound (79), and they obtained as product the thio-benzamide (81), formed by what is probably an electrocyclic ring-opening... 

Raghavendra et al. have synthesized 2-phenyl-2/f-[l,3]thiazino[6,5-i]quinolines (33) in good to excellent yields by one-pot reaction between aldehydes (1) and thio-benzamide using/t-TsOH catalyst under MWI (Scheme 6.14) [53],... 

Dry HGl passed with cooling into a soln. of the equimolar amount of thio-benzamide in acetonitrile, and stored 24 hrs. at room temp. -> thiobenzoyl-acetamidine hydrochloride. Y 68%, F. e. s. J. Goerderler and H. Porrmann, B. 94, 2856 (1961). 

Under treatment with Lawesson s reagent, BSMA benzamide has been converted in good yield into the corresponding thiobenzamide.136 This bis(silyl)thio derivative has been already prepared by silylation of A,A-dimethylbenzothioamide (see Section III.B.l.d). 

Bis[2-[(tetrahydro-2//-pyran-2-yl)thio] phenyljdiazene, B-00458 3,3 -Bis(trifluoromethyl)dithizone, B-00463 A-[3,5-Bis(trifluoromethyl)phenyl]-A-hydroxy-3,5-bis(trifluoromethyl) benzamide, B-00465... 

Hydroxy-5-methylphenyl)azo]phenyi] thio]acetic acid, H-00303 8-Hydroxy-7-[(4-methylphenyl)azo]-5-quinolinesuifonic acid, H-00304 Ar-Hydroxy-A -(2-methylphenyl)benzamide, in H-00109... 

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