New syntheses of cyclopenta[cd]pyrene 3,4-oxide and 4-pyrenylacetic acid

Sahali, Y.; Skipper, Paul L.; Tannenbaum, Steven R.

doi:10.1021/jo00296a065

Cited by 10 publications

(9 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For example, 4-bromopyrene 75 can be treated with n-BuLi followed by CH 3 I or ethylene oxide to yield the corresponding 4-alkylpyrenes 78 and 79. 77,79,80 Similarly, 4-acetylpyrene 76 has been converted into 4-ethynylpyrene 80 by successive Vilsmeier-Haack-Arnold reaction and Bodendorf fragmentation. 53 The HHPy method has been extended to the preparation of pyrene derivatives bearing fused aromatic rings, which are of interest due to their carcinogenic nature and their presence in polluting fumes such as automobile exhausts.…”

Section: The Hexahydropyrene (Hhpy) Methodsmentioning

confidence: 99%

“…79 Finally, 2-(4-pyrenyl)ethanol 79 was oxidised in two steps employing the N-chlorosuccinimide/Me 2 S method followed by Ag 2 O. 80 CPP 90 has also been prepared following a slightly different strategy by oxidizing HHPy at position 1 and condensing the ketone with the Wittig reagent triethyl phosphonoacetate. The resulting product was subsequently hydrogenated, cyclised, decarboxylated and finally rearomatised (Scheme 20).…”

Section: The Hexahydropyrene (Hhpy) Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of substituted pyrenes by indirect methods

2014

View full text Add to dashboard Cite

The pyrene nucleus is a valuable component for materials, supramolecular and biological chemistry, due to its photophysical/electronic properties and extended rigid structure. However, its exploitation is hindered by the limited range of methods and outcomes for the direct substitution of pyrene itself. In response to this problem, a variety of indirect methods have been developed for preparing pyrenes with less usual substitution patterns. Herein we review these approaches, covering methods which involve reduced pyrenes, transannular ring closures and cyclisations of biphenyl intermediates. We also showcase the diverse range of substituted pyrenes which have been reported in the literature, and can serve as building blocks for new molecular architectures.

show abstract

Section: The Hexahydropyrene (Hhpy) Methodsmentioning

confidence: 99%

Section: The Hexahydropyrene (Hhpy) Methodsmentioning

confidence: 99%

Synthesis of substituted pyrenes by indirect methods

2014

View full text Add to dashboard Cite

show abstract

“…[G-3H]CPP was obtained from the NCI chemical repository maintained by Chemsyn Science Laboratories (Lenexa, KS) and purified by HPLC prior to use. Glucose 6-phosphate, d-NADP+, and glucose-6-phosphate dehydrogenase were obtained from Sigma Chemical Co. (St. Louis, MO), trans-3,4-Dihydroxy-3,4-dihydroCPP was prepared by NaBH4 reduction of 3.4-dioxo-3,4-dihydroCPP as described previously (7). The cisdihydrodiol was also isolated from this preparation by HPLC.…”

Section: Methodsmentioning

confidence: 99%

“…trans-3,4-dihydroxy-3,4-dihydroCPP: 8.35-8.05 (m, 8 H), 5.68 (s, 1 H), 5.59 (s, 1 ), 5.19 (s, 2 H)] and by mass spectroscopy of the TMS derivative (M+ 404). 3-Oxo-3.4-dihydroCPP and 3-hydroxy-3,4-dihydroCPP were prepared as described previously (7).…”

Section: Methodsmentioning

confidence: 99%

Microsomal metabolism of cyclopenta[cd]pyrene. Characterization of new metabolites and their mechanism of formation

Sahali

Kwon²,

Skipper³

et al. 1992

Chem. Res. Toxicol.

View full text Add to dashboard Cite

Oxidation of cyclopenta[cd]pyrene (CPP) by mouse and human liver microsomes was used to produce several previously undescribed metabolites, which were separated and isolated by reversed-phase HPLC. Three of these, 3,4-dihydroCPP-c-3,4-diol, 4-hydroxy-3,4-dihydroCPP, and 4-oxo-3,4-dihydroCPP, were fully characterized by GC-MS and UV spectroscopic analysis as well as by total synthesis. Two additional pairs of metabolites were identified as isomeric tetrahydrotetrols and dihydrotriols by GC-MS analysis of their trimethylsilyl derivatives. Their UV spectra were recorded and found to agree with the structure assignments. The tetrahydrotetrols were further characterized by the fact that either 3,4- or 9,10-trans-dihydrodiol could serve as their precursor, indicating that they are the two diastomeric 3,4,9,10-tetrahydroCPP-t-3,4-t-9,10-tetrols. The dihydrotriols were shown to possess t-3,4-dihydrodiol functionality. As found previously using rat liver microsomes, the most abundant metabolite was 3,4-dihydroCPP-t-3,4-diol. It was produced with one enantiomer in severalfold excess over the other, and the major enantiomer was shown to have 3R,4R configuration by exciton chirality circular dichroism. Microsomal oxidation of [4-2H]CPP, which was synthesized for this study, was used to determine the mechanisms of formation of 4-oxo- and 4-hydroxy-3,4-dihydroCPP. The ketone was produced without detectable retention of deuterium label, eliminating the NIH shift as a possible mechanism. The alcohol was shown to arise by NADPH-dependent reduction of both the ketone and another intermediate presumed to be the 3,4-epoxide.(ABSTRACT TRUNCATED AT 250 WORDS)

show abstract

“…The Grignard of 2-brorno-l,4-dimethylnapthalene 3 was prepared by the reaction with Mg in refluxing THF:C6H6 (I : I ) to give 4 which was reacted smoothly with ethylene oxide to give the corresponding alcohol S [13]. The latter on treatent with PBr3 under went conversion to the corresponding bromo derivative, 2-12-(1,4-dimethylnapthyl)]ethylbromide 6 .…”

mentioning

confidence: 99%

A New Synthesis oftrans-3,4-Dihydroxy-anti-1,2-epoxy-1,2,3,4-tetrahydro-7,12-dimethylbenz(a) anthracene

Sharma

1993

Synthetic Communications

View full text Add to dashboard Cite

New syntheses of cyclopenta[cd]pyrene 3,4-oxide and 4-pyrenylacetic acid

Cited by 10 publications

References 1 publication

Synthesis of substituted pyrenes by indirect methods

Synthesis of substituted pyrenes by indirect methods

Microsomal metabolism of cyclopenta[cd]pyrene. Characterization of new metabolites and their mechanism of formation

A New Synthesis oftrans-3,4-Dihydroxy-anti-1,2-epoxy-1,2,3,4-tetrahydro-7,12-dimethylbenz(a) anthracene

Contact Info

Product

Resources

About