Malononitrile benzylidene

Some TICT-forming fluorescent probes containing the / j - /V. /V - cl i a I k I a m i n o benzylidene malononitrile motif (usually related to 30 in Fig. 11) have been applied to monitor and quantify polymerization reaction, crosslinking, chain relaxation,... 

Nucleophilic attack of hydroxide ion on the a-carbon atom, with subsequent cleavage of the Ca—Cp bond, has been proposed to account for the kinetics of retro-aldol reaction of substituted benzylidene malononitriles with hydroxide ion in 90%... 

The 4-aminopyrimidines 367 and 368 were prepared by the reaction of the benzylidene malononitriles with thiourea or S-methylisothiourea, respectively. Nucleophilic substitution at the 2-position of 368 with hydrazine gave the 2-hydrazino derivative 369, whose treatment with carbon disulfide yielded the triazolopyrimidine 373 rather than its isomeric compound [83ZN(B)1686]. Heating 369 with benzoyl chloride in anhydrous dioxane,... 

CS. A US CWS code designation for o-ckloro-benzylidene malononitrile (called 2-Chlor -benzylidenmalonsaure-dinitril in Ger), Cl-C6H4.CH C(CN)2 col crysts (from ale,... 

Various unsaturated compounds, such as CO2, isocyanates and aldehydes, undergo Pd-catalysed cycloaddition with vinyl epoxides. Reaction of CO2 with 127 affords cyclic carbonates 128 with retention of the configuration at C(3), offering a method of cis hydroxylation of epoxides [66], and has been used for the synthesis of the side-chain unsaturated (—)-exo-brevicomin (129) [67], The tetrahydrofuran 131 was prepared by [3+2] cycloaddition of activated alkenes such as benzylidene malononitrile (130) with vinyl epoxide via Michael addition and allylation [68],... 

Recently Shi et al. (239) reported the synthesis of a 432-member focused hbrary LIO as a source of tyrosine kinase inhibitors using benzylidene malononitriles, or tyr-phostins, as structural motifs to design the library. Both the general tyrphostin structure (7.61) and an example of an active compound on a specific tyrosine kinase (7.62) are reported in Fig. 7.37. 

Reaction of 91 and 92 with 88 furnishes the arylidene products 89 [81S635 84ZN(B)824 87IJC(B)216], whereas the condensation of 92a with cyanoacetic acid hydrazide yields the parent bicyclic product 93 (84JHCI885). Arylidene product 89 is presumed to have been obtained via the intermediate 5-benzylidene derivative of 91 and 92 formed by the addition of the active methylene in 91 and 92 to the activated double bond of benzylidene malononitrile with concomitant elimination of malononi-trile, which subsequently adds to the activated double bond of the interme-... 

AODCST, 2-[4-bis(2-methoxyethyl)amino]benzylidene malononitrile PTPDac-BA2, copolymer, 65% wt N-(4-acryloyloxymethylphenyl)-N -phenyl-N,N -bis(4-methylphenyl)-[ 1,1 -biphenyl]-4,4 -diamine, 35% wt A-butylacetate DOP, dioctyl phthalate DRl-DCTA, 4,4 -di(carbazol-cl-yl)-4"-(2- N-ethyl-N-[4-(4-nitrophenyldzo)phenyl]amine ethoxy)-triphenylamine other abbreviations are defined in the text and Figures, quantum effieieney of mobile charge photogeneration has been estimated where necessary, °a relative static dielectric constant of 3 and a linear electro-optic response have been assumed. 

Ballantyne, B., Gazzard, M.F., Swanston, D.W., and Williams, P., The ophthalmic toxicology of o-chloro-benzylidene malononitrile (CS), Arch. Toxicol, 32, 149-168, 1974. 

Figure 2. Effect of concentration of 2-chloro-benzylidene malononitrile (CS) dissolved in saline on the time to onset (latency) of sensation following the application of 0.01 ml droplets to the surface of the cornea of a human volunteer subject (data after Ballantyne and Swanston, 1973)...

Figure 9. Structural formula of the RCA 2-chloro-benzylidene malononitrile (CS)...

Ballantyne B and Johnson WG (1974b). o-Chloro-benzylidene malononitrile (CS) and the healing of cutaneous injuries. Med Sci Law, 14, 93-97. 

Amino-4-aryl-3-cyano-7,7-dimethyl-5,6,7,8-tetrahydro-4H-benzo[f>]pyran 281 were reacted with benzylidene malononitrile in the presence of piperidine at 160 °C to afford pyrido[3,4-frJqu inclines 341 (89JPR971) (Scheme 65). 

Pyrimido[4,5-fr]quinolines 344 were obtained from 2-amino-3-cyanoqui-noline 280 (R = Ar1) upon reaction with benzoyl isothiocyanate (96IJC(B)608) (Scheme 67). Reaction of enamine 31 (R = o-CNC6H4) with benzylidene malononitrile in the presence of DBU gave the pyrimidoquinoline 345 via the respective quinoline 280 (01ARK73). A series of pyrimidoquinolines were prepared by cyclization of the... 

In contrast, when benzylidene malononitriles 443 (X = CN) were melted with dimedone in stoichiometric amounts without catalyst at 97-130 °C for 1 h, it gave 444 that afforded quantitative yields of 281... 

Solvent Effects on k0. Only a few studies so far allow an assessment of solvent effects of k0. The change from water to 50% (CH3)2SO-50% water enhances log k0 from 2.10 to 2.55 in the reaction of piperidine and morpholine with P-nitrostyrene (22) and from 4.55 to 4.94 with benzylidene-malononitrile (C. F. Bernasconi and R. B. Killion, unpublished results). On the other hand, the change from water to acetonitrile either leaves k0 unaffected or even decreases it slightly in the reaction of benzylidene-substituted Meldrum s acid with the same amines (23, 24) the uncertainty is due to a lengthy extrapolation in water that renders k0 uncertain in this solvent. 

SYNONYMS o-chlorobenzal malononitrile, 2-chlorobenzal malononitrile, 2-chloro-benzylidene malononitrile, 2-chlorobmn, beta, beta-dicyano-o-chlorostyrene, propanedinitrile ((2-chlorophenyl)methylene). 

Benzylidene malononitrile [2700-22-3] M 154.2, m 83-84 , 87°. Reciystallise the nitrile from EtOH... 

Dihexadeeyl phosphate (DHP) [2197-63-9] M 546.9, m 75 , pK t l-2. Recrystallise it from MeOH. Solutions of DHP were made in CHCI3 or CH2CI2 for making vesicles. It has been used for making surfactant vesicles in studies of the viscosity-dependent variations of the fluorescence yield ( )f and the polarity induced shift of the emission band maximum F(max) of a derivative of a [)7-(dialkylamino)benzylidene]malononitrile [74677-08-0] fluorescence probe. Lcka.cJAm Chem Soc 106 4387 1984]. [Beilstein 1IV 1880.]... 

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