Synthesis of Pyromellitonitrile and Related Compounds<sup>1</sup>

Lawton, Emil A.; Mcritchie, D. D.

doi:10.1021/jo01083a008

Cited by 61 publications

(12 citation statements)

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“…1,3,5-TrCB [56], 1,2,4-TrCB [56], DCN [57], DCP [10], DCP-Me [10], ME [58], PME [11] and OXA [59] were obtained by known procedures. Since oxygen could interact with the photogenerated radical anions, resulting in a back oxidation [6], all of the experiments were carried out in freeze–pump–thaw deoxygenated solutions, except where otherwise noted.…”

Section: Methodsmentioning

confidence: 99%

Spectroscopic characterization of photoaccumulated radical anions: a litmus test to evaluate the efficiency of photoinduced electron transfer (PET) processes

Fagnoni¹,

Protti²,

Ravelli³

et al. 2013

Beilstein J. Org. Chem.

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SummarySteady-state irradiation in neat acetonitrile of some aromatic nitriles, imides and esters (10−5–10−3 M solution) in the presence of tertiary amines allowed the accumulation of the corresponding radical anions, up to quantitative yield for polysubstituted benzenes and partially with naphthalene and anthracene derivatives. The condition for such an accumulation was that the donor radical cation underwent further evolution that precluded back electron transfer and any chemical reaction with the radical anion. In fact, no accumulation occurred with 1,4-diazabicyclo[2.2.2]octane (DABCO), for which this condition is not possible. The radical anions were produced from benzene polyesters too, but decomposition began early. Ipso substitution was one of the paths with secondary amines and the only reaction with tetrabutylstannane. The results fully support the previously proposed mechanism for electron transfer (ET) mediated photochemical alkylation of aromatic acceptors via radical ions and radical intermediates.

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Section: Methodsmentioning

confidence: 99%

Spectroscopic characterization of photoaccumulated radical anions: a litmus test to evaluate the efficiency of photoinduced electron transfer (PET) processes

Fagnoni¹,

Protti²,

Ravelli³

et al. 2013

Beilstein J. Org. Chem.

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“…Compounds 5a and 5b were synthesized from corresponding phthalic anhydrides ( 3a ) or phthalimide ( 3b ) through phthalazine ring formation by hydrazine monohydrate and chlorination by phosphorus oxychloride. Compound 5c was synthesized from 2-chloro-5-trifluoromethylbenzoic acid ( 1 ) through the corresponding phthalimide ( 3c ) by the method of Lawton and McRitchie . Compound 5d was prepared through the corresponding phthalimides synthesized by means of the Sandmeyer reaction of 4-aminophthalimide ( 2 ).…”

Section: Chemistrymentioning

confidence: 99%

4-Benzylamino-1-chloro-6-substituted Phthalazines: Synthesis and Inhibitory Activity toward Phosphodiesterase 5

et al. 1998

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We synthesized various 4-benzylamino-1-chloro-6-substituted phthalazines (15) and 4-benzylamino-1-chloro-7-substituted phthalazines (16) and evaluated their inhibitory activity toward phosphodiesterase 5 (PDE5) purified from porcine platelets. The PDE5-inhibitory activities of 15 were greater than those of the isomers (16). The preferred substituent at the 4-position of phthalazine was a (3-chloro-4-methoxybenzyl)amino group, and those at the 6-position were cyano, nitro, and trifluoromethyl groups. Compounds 15a (IC50 = 4.8 nM), 15f (3.5 nM), and 15i (5.3 nM) were more potent inhibitors than E4021 (8.6 nM). Compounds 15a and 15f also showed vasorelaxant activity in isolated porcine coronary arteries precontracted with prostaglandin F2alpha (10(-5) M). The EC50 values for vasorelaxant action of 15a, 15f, and E4021 were 150, 160, and 980 nM, respectively. These results show that novel PDE5 inhibitors possessing a potent vasorelaxant effect may exist among phthalazine derivatives.

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“…Tatemoto (unpublished). He has found that conversion of the amide to the nitrile by use of SOCl, and dimethylformamide (Lawton & McRitchie, 1959) followed by the addition of a tertiary alcohol to the nitrile (Ritter & Minieri, 1948;Sjoberg, 1968) offers some promise. The resulting N-alkylamide grouping is (relatively) stable to alkali (Ritter & Minieri, 1948) and it seems to be possible to carry out alkaline hydrolysis of the peptide chain, followed by identification-for instance as its dansyl derivative-of the N-alkylamide derivative of the amino acid amide originally present at its C-terminus.…”

Section: Smentioning

confidence: 99%

Further Investigations on Intestinal Hormonal Polypeptides

Mutt

1976

Clinical Endocrinology

117

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Attempts are described to identify additional polypeptides of hormonal nature in a concentrate of intestinal polypeptides shown previously to contain secretin, cholecystokinin-pancreozymin (CCK), motilin, gastric inhibitory polypeptide (GIP), vasoactive intestinal polypeptide (VIP), enteroglucagon and chymodenin. The probable amino acid sequence of a variant form of CCK is disclosed. The possibility of using characteristic fragments of polypeptides for the quantitation of the polypeptides themselves in crude preparations is briefly discussed.

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Synthesis of Pyromellitonitrile and Related Compounds¹

Cited by 61 publications

References 0 publications

Spectroscopic characterization of photoaccumulated radical anions: a litmus test to evaluate the efficiency of photoinduced electron transfer (PET) processes

Spectroscopic characterization of photoaccumulated radical anions: a litmus test to evaluate the efficiency of photoinduced electron transfer (PET) processes

4-Benzylamino-1-chloro-6-substituted Phthalazines: Synthesis and Inhibitory Activity toward Phosphodiesterase 5

Further Investigations on Intestinal Hormonal Polypeptides

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Synthesis of Pyromellitonitrile and Related Compounds1

Cited by 61 publications

References 0 publications

Spectroscopic characterization of photoaccumulated radical anions: a litmus test to evaluate the efficiency of photoinduced electron transfer (PET) processes

Spectroscopic characterization of photoaccumulated radical anions: a litmus test to evaluate the efficiency of photoinduced electron transfer (PET) processes

4-Benzylamino-1-chloro-6-substituted Phthalazines: Synthesis and Inhibitory Activity toward Phosphodiesterase 5

Further Investigations on Intestinal Hormonal Polypeptides

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Synthesis of Pyromellitonitrile and Related Compounds¹