Some Barbituric Acids Containing the 2-Methylallyl Group

Doran, Wilbur J.; Shonle, H. A.

doi:10.1021/ja01288a019

Cited by 16 publications

(7 citation statements)

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“…Work-ups gave the target complexes 4a-d as analytically pure pink solids in 64-78 % yields. They were characterized by NMR spectroscopy ( 1 H, 13 C, 31 P, 19 F) and mass spectrometry, as summarized in the Experimental Section. Most data were routine, combining features previously observed with Grubbs second generation catalyst 2 and metal complexes of 1a-d.…”

Section: Synthesis and Characterization Of New Metathesis Catalystsmentioning

confidence: 99%

“…Chemicals were treated as follows: ether, toluene, hexanes, distilled from Na/benzophenone; perfluoro(methylcyclohexane) (CF 3 C 6 F 11 ; ABCR), CF 3 C 6 H 5 (ABCR), distilled from CaH 2 ; diethyl diallylmalonate (5; Lancaster), tridecane (Aldrich), perfluoro(2-butyltetrahydrofuran) (C 8 F 16 O; Apollo), perfluorohexane (C 6 F 14 ; Fluorochem), 1H,1H-perfluoroheptanol (CF 3 A C H T U N G T R E N N U N G (CF 2 ) 5 CH 2 OH; ABCR), CD 2 Cl 2 (Cambridge Isotope or Aldrich) and other solvents, used as received. Diethyl 2-allyl-2-methallylmalonate (7), [31] N,N-diallyltosylamide (9) [32] and N-allyl-N-methallyltosylamide (11) [6] were synthesized by literature procedures.…”

Section: Experimental Section General Remarksmentioning

confidence: 99%

“…One experiment is identical to C in Figure 2 Figure 4 (A): A two-neck flask was charged with 7 (0.0524 g, 0.206 mmol) [31] and hexadecane (0.0530 g, 0.234 mmol), and flushed with nitrogen. Freshly distilled CH 2 Cl 2 was added (4.0 mL, giving a 0.052 M solution).…”

Section: Experiments In Figurementioning

confidence: 99%

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Syntheses and Reactivity of Analogues of Grubbs’ Second Generation Metathesis Catalyst with Fluorous Phosphines: A New Phase‐Transfer Strategy for Catalyst Activation

Costa

Gladysz

2007

Adv Synth Catal

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(4a-d, 64-78 %), which are analogues of Grubbs second generation alkene metathesis catalyst. Complexes 4a,b are effective catalysts for conversions of 1,6-dienes to cyclopentenes under monophasic and biphasic conditions in CH 2 Cl 2 and CH 2 Cl 2 /fluorous solvent mixtures. The latter generally exhibit rate accelerations, which are believed to arise from phase transfer of the dissociated fluorous phosphine, allowing the substrate to better compete for the fourteen valence-electron intermediate. Only modest effects are observed when Grubbs second generation catalyst is similarly reacted. The most fluorophilic catalyst, 4c, can be recycled by extracting the reaction mixtures with perfluoro(methylcyclohexane).

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Section: Synthesis and Characterization Of New Metathesis Catalystsmentioning

confidence: 99%

Section: Experimental Section General Remarksmentioning

confidence: 99%

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Syntheses and Reactivity of Analogues of Grubbs’ Second Generation Metathesis Catalyst with Fluorous Phosphines: A New Phase‐Transfer Strategy for Catalyst Activation

Costa

Gladysz

2007

Adv Synth Catal

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“…These were purified by distillation i n nacuo. The preparation of some of these malonates has been described (18). Diethyl methylmalonate (Sapon), diethyl ethylmalonate (Distillation Products Industries), diethyl n-propylmalonate (Sapon), ancl diethyl phenyllnalonate (Benzol Products) were used without further purification.…”

Section: Preparation Of Imono-and Di-substituted I~~ulonutesmentioning

confidence: 99%

Tetrahydrofurans: I. 2,2-Dimethyl-4-Substituted-4-Hydroxymethyltetrahydrofurans and Related Compounds

Wasson¹,

Gleason²,

Levi³

et al. 1961

Can. J. Chem.

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Substituted methallyl~ualonic esters ( I ) were reduced with lithi~lm aluminum hydride to the corresponding 2-methallyl-1,3-propanediols (11). These diols I1 ~lnderwent cyclization on treatment with a ~niileral acid to the isomeric 2,2-di1nethyl-4-substituted-4-hydroxy1neth~l-tetrahydrofurans ( I V ) . I1 and IV were converted to the respective carbamates 111 and V, which exhibited pharn~acological activity. The assigned structures of the cyclic compounds While preparing 2,2-dis~1bstit~1tecl-1,3-propanediol dicarbamates, it was noted that an interinecliate, 2-allyl-2-metl1all)il-1,3-propanediol (IIe), was labile to hydrochloric acid affording a compouncl assuinecl to be 2,2-climetl1yl-4-allyl-4-hydrox~~metl1yltetral1ydro-furall (IVe). This assignment, macle by analogy with a lcno\vn method of preparing tetrahydrofurans (1-3), was subsequei~tly verified. Since IVe possessed interesting pharmacological activity it was cleciclcd to prepare additional 2,2-diinethyl-4-~~1bstituted-4-hydroxymethyltetrahydrofura~~s (IV). Thus substituted inetl~allyln~alonic esters (I) were reduced to the corresponding 2-substit~1ted-2-methal~yl-1,3-propanediols (11) and subsecluently cyclizecl by means of mineral acid. Both I1 ancl IV were convertecl to the YI* corresponding carbamates I I I and V (Fig. 1).:-

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“…The diol V was obtained by reduction (4) of diethyl dimethallylrnalonate (11) with lithium aluminum hydride (5). The ring-closure was vigorously exothermic, even with only a trace of acid present, requiring a solvent to modify the reaction temperature.…”

mentioning
confidence: 99%

Tetrahydrofurans: Ii. Spiro Compounds Containing the Tetrahydrofuran Ring
Wasson¹,
Kernan²,
Parker³
1963
Can. J. Chem.
3
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1
0
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3-Allyl-2-methallyl-1,3-propat~ediol (IV) and 2,2-dimethallyl-1,3-propailediol (V) mere cyclized in the presence of mineral acid to give 3,3,8-trimethyl-2,7-dioxaspiro(4.4)nonane (VIII) and 3,3,8,8-tetramethyl-2,7-dioxaspiro(4.4)nonane (IX), respectively. Similarly, 2-methallyl-2-(3-methyl-2-butenyl)-1,3-propanediol (\'I) afforded 3,3,8,8-tetramethyl-2,7-dioxaspiro(4.5)decane (X). The diol VI was derived from diethyl methallylmalonate by condensation with 3-methyl-2-butenyl bromide, followed by reduction of diethyl tnethallyl(3-methyl-2-buteny1)malonate (111) with lithium aluminum hydride. The assigned structures of the spiro compounds were supported by infrared and nuclear magnetic resonance spectral analyses. DISCUSSION

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Some Barbituric Acids Containing the 2-Methylallyl Group

Abstract: Substituted Average Z-methylallyl-% Nitrogen-M. A . D ,h M. L. D', duration of barbituric acid M. p ~ 0C.f Calcd. Found mg./kg. mg./kg. M. A. D , mio.

Cited by 16 publications

References 0 publications

Syntheses and Reactivity of Analogues of Grubbs’ Second Generation Metathesis Catalyst with Fluorous Phosphines: A New Phase‐Transfer Strategy for Catalyst Activation

Syntheses and Reactivity of Analogues of Grubbs’ Second Generation Metathesis Catalyst with Fluorous Phosphines: A New Phase‐Transfer Strategy for Catalyst Activation

Tetrahydrofurans: I. 2,2-Dimethyl-4-Substituted-4-Hydroxymethyltetrahydrofurans and Related Compounds

Tetrahydrofurans: Ii. Spiro Compounds Containing the Tetrahydrofuran Ring

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