3-Phenylsulfonyl-4,5-dihydro

Phenol 6-Hydroxymethyl-4-methyl-2-thiocyanatomethyl- IX, 858 3H-Pyrrol 3-Phenylsulfonyl-4,5-dihydro-Ell, 1254 (C,C-Aufbau) Thiophen 4-Cyan-2-ethoxycarbonyl-5-ethyl-3-hydroxy- E6a, 297 [HS-CH2-COOR + RO-C(C2H 5) = C(CN) - COOR]... 

To a stirred ice-cold solution of ethyl 3,6-dihydro-5-hydroxy-8-methyl-6-(phenylsulfonyl)benzo[l,2-b 4,3-b ]dipyrrole-l-carboxylate (368 mg, 0.85 mmol) in TEA (3ml) was added EtjSiH (1.5 ml), After 15 min the solution was allowed to come to room temperature and stirred for an additional 2h. The solution was evaporated in vacuo and the residue dissolved in CH2CI2 (10 ml), washed.with aq. NaHCOj and dried over MgS04. The solution was mixed with AcjO (1ml) and CH2C12 (1ml) and kept at room temperature for 2 h. The reaction mixture was evaporated and the residue purified by chromatography on silica gel using CHjClj-EtOAc (3 1) for elution. The product (271 mg) was obtained in 71 % yield. 

R,3S,6S)-3,6-dihydro-3-hydroxy-6-isopropo.xy-2-[(S)-I-methvl-2-(phenylsulfonyl)ethyl]-2Vl-pyran yield 80% d.r. (anti/syn) 91 8... 

C H 7N02 2164-42-3) see Guanoxan ll,12-dihydro-ll-(phenylsulfonyl)retinol acetate... 

Synthetic Method 9 N-[8-bis(2-cyanoethyI) -9-[4- (phenylsulfonyl) -benzoyl]-9, 10-dihydro-1 0-phenyl-2-phenazinyl]-4-phenylsulfonylbenzamide (53) (procedure from US. Patent 4,889,932).18 A 3-liter round-bottom flask fitted with a mechanical stirrer was loaded with 16.6 g (0.066 mol) of 4-[di(2-cyanoethyl)amino]aniline in 800 ml of deionized water. A 10% excess of aniline (13.56 g, 0.1456 mol) and 100ml of deionized water were added to the mixture. The mixture was cooled to 0°C in an ice bath, and... 

Benzothiadiazoles 3 have been extensively studied. Fully aromatic mesoionic compounds such as 4 continue to be synthesized. A number of examples of 4,5-dihydro-l,2,3-thiadiazole derivatives such as compound 5 <1993JOC82> and more recently the phenyl derivative 6 <2003RJ01501> have been reported. The corresponding 2,3-dihydro-l,2,3-thiadiazoles have also been reported and Hurd and Mori reported the N-Z phenylsulfonyl derivative 7. The electron spin... 

Products isolated from the thermal fragmentation of A-arylbenzamide oximes and A-arylbenzamide O-phenylsulfonyl oximes have been accounted for by invoking a free-radical mechanism which is initiated by the preferential homolysis of the N-O bond." Time-resolved IR spectroscopy has revealed that photolysis of A, A -diphenyl-l,5-dihydroxy-9,10-anthraquinone diimine affords acridine-condensed aromatic products via excited-state intramolecular proton transfer." The absolute and relative rates of thermal rearrangements of substituted benzyl isocyanides have been measured,and it has been found that the relative rates are independent of temperature and exhibit excellent Hammett correlations. Thionitrosoarene (25), thought to be generated by desulfurization of the stable A-thiosulfinylaniline (24), has been established" " as an intermediate in the formation of 3,3a-dihydro-2,l-benzisothiazole (26) from o-alkylthionitrosoarene (24). 

Die Reduktion von a-Nitro-sulfonen mit 3-Aminocarbonyl-1-benzyl-1,4-dihydro-pyridin gelingt auch unter Belichtung in sehr guten Ausbeuten z.B. reagiert l-Nitro-2-phenyl-1-phenylsulfonyl-ethan zu 2-Nitro-l-phenyl-ethan (62%) ... 

Treatment of 3,6-diphenyl-l,2-di(phenylsulfonyl)-l,2-dihydro-l,2,4,5-tetrazine (79) with concentrated sulfuric acid affords 3,6-diphenyl-l,4-dihydro-l,2,4,5-tetrazine (80) in good yield (79BCJ483). 

Thermolysis of 3,6-diphenyl-l,4-di(phenylsulfonyl)-l,4-dihydro-l,2,4,5-tetrazine (127) in boiling toluene gives benzenesulfonic anhydride (128), phenyl benzenethiosulfonate (129), small amounts of diphenyl disulfide (130), 3,6-diphenyl-l,2,4,5-tetrazine (51) and a rearrangement product, 3,6-diphenyl-l,2-di(phenylsulfonyl)-l,2-dihydro-l,2,4,5-tetrazine (79) (79BCJ483). 3,6-Disubstituted hexahydro-1,2,4,5-tetrazines (132) afforded aldehyde hydrazones (133) when heated at their melting point (63AG1204). 

This procedure is also efficient for the synthesis of other fused tetrazoles, such as ethyl l,5-dihydro-5-oxo-7-phcnyl-8-(phenylsulfonyl)tetrazolo[ 1,5- pyridine-6-carboxy late <2000J(P1)3686>. At the same time, the unexpected azido-tetrazolo tautomerization and reversible tetrazolo transformation of 3,6-diazido-l,2,4,5-tetrazine are remarkable compared to all other polyazido heteroaromatic high-nitrogen C-N compounds <2005JA12537>. 

Ethyl l-cyclopropyl-4-oxo-7-phenylsulfonyl-6-trifluoromethyl-l,4-dihydro-l,8-naphthyridine-3-carboxylate (7) gave the crude ester (8, R = Et) (piperazine, MeCN, 20°C), characterized after saponification to l-cyclopropyl-4-oxo-7-(piperazin-l-yl)-6-trifluoromethyl-l,4-dihydro-1,8-naphthyri dine-3-car-boxylic acid (8, R = H) (NaOH, EtOH 37% overall).1167... 

Phenylsulfonyl)furo[2,3- ]quinoline and its parent unsubstituted heterocycle were found to have very similar absorption maxima hence, the sulfone group does not provide an additional conjugative effect <83JOC774>. In addition, furo[2,3-/ quinoline and its isomeric furo[3,2-< ] counterpart were found to exhibit UV absorption maxima that are almost identical. An absorption maximum at 435 nm consistent with the presence of a 2H-1,4-benzothiazine chromophore was one of the key pieces of data that enabled the structure determination of compounds based upon the new 1,2-dihydro-3//,8//-pyrrolo[2,3-/z][l,4]benzothiazine skeleton <87T5357>. The UV spectrum of l,4-benzodioxano[6,7-c]furoxan was found to exhibit four characteristic band maxima in the 350-480 nm region <88JHC803>. 

Most fused benzene rings are stable toward nucleophilic attack but exceptions are known for highly electron-deficient benzazoles having o-quinonoid structures. Thus, sulfur nucleophiles attack 27/-benzimidazole-2-spirocyclohexane 556 via an initial Michael-type 1,4-conjugate addition, followed by a prototropic shift in the adduct 557. When the nucleophile is electron withdrawing (e.g., phenylsulfonyl), 1,3-dihydro products 558 are isolated. If the nucleophile is electron donating, the adducts are oxidized in situ to 559. 

Oxazol 5-Methyl-4-(4-methyl-phenylsulfonyl)-4,5-dihydro-EI9d, 679 (R-NC +... 

Indene reacts with benzenesulfonyl chloride in the presence ofcopper(ll) chloride in a stereoselective manner to afford tr fl.r-l-chloro-2,3-dihydro-2-phenylsulfonyl-1 7/-indene (3)127. 

Dihydro-l,5-dimethyl-5- (4-phenylsulfonyl)phenyl -5/t-pyrano 3,2-[Pg.1127]

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