Cyclohexyl-6- -dione

A variety of 2,5-dialkylfurans are available via the Paal-Knorr condensation cyclization is possible for both hindered and unhindered 1,4-diketones. Fleming prepared 2-cyclohexyl-5-methylfuran (31) in 91% yield via treatment of dione 30 with catalytic p-toluenesulfonic acid in refluxing benzene. Using the same methodology, Denisenko synthesized furan 33 in 35% yield from the corresponding dione (32). ... 

Nitration of 2-cyclohexyl-8-hydroxy-2,3,4,6,11,11 u-hexahydro-1 //-pyra-zino[l,2-6]isoquinoline-l,4-dione with 70% HNO3 at room temperature for 30 min afforded an 1 1 mixture of 7- and 9-nitro derivatives (98MIP7). 

Spiro[4.5]decane-l,4-dione and Ethyl 4-Cyclohexyl-4-oxobutanoate... 

Isocyanide, benzyl, 55, 98 Isocyanide, butyl-, 55, 98 Isocyanide, cyclohexyl-, 55, 98 ISOCYANIDE, 1,1-dimethylethyl- [Isocy-amde, tert-butyl-], 55,96 Isocyanide, dodecanyl- 55,98 Isocyanide, ethyl- 55,98 Isocyanide, methyl-, 55, 98 Isocyanide, phenyl-, 55, 98 1//Isoindole 1,3(2//) dione, 2 amino [Phthahmidc, N-amino-], 55, 115 1//-ISOINDOLE-1,3(2//)-DIONE, trans-( )-2-(2,3-diphenyl-l-aziridinvl)-[Azindine, frans-2,3-diphenyl-l-phthalimido-], 55, 115 ISOXAZOLE, 3-(4-chlorophenyl)-5-(4-methoxy phenyl)-, 55, 39 Isoxazole 5-(4-chlorophenyl)-3-(4-meth-oxyphenyl)-, 55, 42... 

CN [liP,16p,21(tranj)]-21-[[[4-[(acetylamino)methyl]cyclohexyl]carbonyl]oxy]-9-chloro-l 1,17-dihydroxy-16-methylpregna-1,4-dicne-3,20-dione... 

The formation of l,3,4-triarylpyrroline-2,5-diones from the reaction of diphenylcyclopropenone and N-sulfinylarylamines with nickel carbonyl has been described earlier (see Scheme 36 in Section IV,A,2).64 In contrast with this result, 2,4,5-triphenyl-3-isothiazolone 1-oxide is produced in this type of process using iron pentacarbonyl, and the analogous cyclohexyl derivative is formed in a nickel carbonyl-mediated reaction (Scheme 115).64 It is probable that metallocyclic species (cf. 93) are intermediates in these transformations. 

Reaction of 3-alkylamino-6,8-dimethylpyrimido[4,5-c]pyridazin-5,7-diones 80 with cyclohexyl and cycloheptylamines afforded novel cycloalkano bis(pyrrolo[2,3-c]pyrimido[5,4-e]pyridazines 81 <06T652>. 

Hexazinone is subject to microbial degradation (Rhodes, 1980 Feng, 1987). Metabolites identified in soils, alfalfa, and/or sugarcane include 3-(4-hydroxycyclohexyl)-6-(dimethylamino)-1 -methyl-s-triazine-2,4 (1 //, 3/7) dione, 3-cyclohexyl-6- (methylamino) -1 -methyl-5-triazine-2,4-... 

Feng (1987) monitored the persistence and degradation of hexazinone in a silt loam soil 104 d after treatment of the herbicide. After 104 d, 66% of the hexazinone degraded via hydroxylation to form the major metabolite 3-(4-hydroxycyclohexyl)-6-(dimethylamino)-l-methyl-s-triazine-2,4(l//,3//)dione (30-50% yield). A minor metabolite, 3-cyclohexyl-6-(methylamino)-1-methyl-s-triazine-2,4(1//,3//)-dione, forming via demethylation, accounted for only 0-12% of the applied herbicide. Hexazinone and its metabolites were not detected in soils at depths of 15-30 cm. 

Cyclohexyl ine, 52, 727 reaction with acetaldehyde, 50,67 Cyclooctatretraene, chlorination, 50, 36 reaction with mercuric acetate, 50, 24 CYCLOOCTENE, 1-NITRO, 50,54 CYCLOPENTANECARBOXALDE-HYDE, l-PHENYL-,51,24 Cyclopentane-1,3-dione, 52,4 CYCLOPENTYLAMINE, 1-PHENYL-, 51,45... 

Several 1,4-disubstituted derivatives of the dication, 63, were successfully prepared. The 1,4-diphenyl, 1,4-dimethyl, 1,4-dicyclopropyl-substituted derivatives of carbodication 63 (65, 66, and 67) are exceptionally stable. The 1,4-dimethyl-1,4-cyclohexyl dication, devoid of the adjacent cyclopropyl groups, could not be prepared. The carbocationic center in all these dications are somewhat shielded as compared to their monocations. The C NMR chemical shifts of the carbocationic centers for the dications 65, 66, and 67 are 235.4, 293.4, and 260.8 ppm, respectively. The diprotonated ann -tricyclo(5.1.0.0 )octa-2,6-dione, 68, may be treated as a dicarboxonium ion, instead of dihydroxy dicarbenium ion, since the cabronyl carbon is shielded by only 25.2 ppm, much smaller than that observed for the protonated cyclohexanedione (34 ppm). The para carbons of the phenyl substituents in carbodication 65 are relatively shielded by about 5 ppm from that of the parent l,4-diphenylcyclohexane-l,4-diyl dication showing relatively less delocalization of the charge into the aromatic rings. 

Changing the nature of the triazine substitution pattern to the l,3,5-triazine-2,4-dione system leads to another series of herbicides, of which the best example is hexazinone (1) (75USP3902887). It is built up from cyanamide which is converted in several steps to the guanidine (2). Reaction with cyclohexyl isocyanate then gives an intermediate which can be cyclized to hexazinone (Scheme 2). 

RING EXPANSION AND CLEAVAGE OF SUCCINOIN DERIVATIVES SPIR0C4, 5]DECANE-1,4-DIONE AND ETHYL 4-CYCLOHEXYL-4-0X0BUTAN0ATE (Cyclohexanebutanoic acid, y-oxo-, ethyl ester)... 

Fluorination of 9-benzyloxy-2-(4-fluorobenzyl)-6-methoxy-3,4-dihy-dro-lH,8H-pyrido[l,2-a]pyrazine-l,8-dione with Selectfluor in the presence of Ce2C03 in MeCN at ambient temperature for 6 h provided 7-fluoro derivative. Reaction of 6-bromo-3,4-dihydro-lH,8H-pyrido[1,2-a]pyra-zine-l,8-diones with phenol cyclohexyl-, and cyclopropylmethanols in the presence of Ce2C03 in DMF in a sealed tube at 25-60 °C for 12-24 h afforded 6-phenoxy, 6-cyclohexyl-, and 6-cyclopropylmethoxy derivatives, respectively (06WOP2006/066414). 

IUPAC A2-isopropyl-A4-methyl-6-methylthio-1,3,5-triazine-2,4-diamine N2-(, 2-dimethylpropyl)-A4-cthyl-6-methylthio-1,3,5-triazine-2,4-diamine 3-cyclohexyl-6-diethylamino-1 -methyl-1,3,5-triazine-2,4(1//,3//)-dione... 

One example has been reported 1,3-dipolar cycloaddition of A-phenylbenzonitrile imide or benzonitrile oxide to the carbonyl group of a 3-iminopyrido[3,4-/>]pyrazine-1,4-dione gave (167 R1 = cyclohexyl, R2 = Ph) and (168 R1 = cyclohexyl, R2 = Ph), respectively (86LA938). 

SYNS 3-CYCLOHEXYL-6-piMETHYLAMINO)-l-METHYL-s-TRIAZINE-2,4(lH,3H)-DIONE 3-CYCLO-HEXYL-6-(DIMETHYLAMINO)-l-METHYH,3,5-TRIAZINE-2,4(lH,3H)-DIONE DPX 3674 VELPAR VELPAR WEED KILLER... 

CYCLOHEXYL-6-(DIMETHYLAMINO)-l -METHYL-s-TRIAZINE-2,4(lH,3H)-DIONE see HFA300... 

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