Syntheses of calix[4]pyrroles by amberlyst-15 catalyzed cyclocondensations of pyrrole with selected ketones.
نویسندگان
چکیده
A facile and efficient protocol is reported for the synthesis of calix[4]pyrroles and N-confused calix[4]pyrroles in moderate to excellent yields by reaction of dialkyl or cycloalkyl ketones with pyrrole catalyzed by reusable Amberlyst(TM)-15 under eco-friendly conditions.
منابع مشابه
Molecular recognition and self-assembly special feature: Self-assembly of dimeric tetraurea calix[4]pyrrole capsules.
Calix[4]pyrroles having extended aromatic cavities have been functionalized with 4 ureas in the para position of their meso phenyl substituents. This elaboration of the upper rim was completed in 2 synthetic steps starting from the alpha,alpha,alpha,alpha-tetranitro isomer of the calix[4]pyrrole obtained in the acid catalyzed condensation of p-nitrophenyl methyl ketone and pyrrole. In dichlorom...
متن کاملResults and Discussions
Calix (4) pyrroles are macromolecules structurally related to porphyrins, they exhibit exceptional chemical and physical properties that have suggested a vast number of potential applications in host-guest chemistry. In recent years, calix (4) pyrroles have attracted a lot of attention because of their properties as binders of anions, transition metals, and neutral substrates and their new appl...
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One pot synthesis of terpyrromethanes (3a) and [di(1H-pyrrol-2-yl)methyl]heteroarenes (3b-m) has been delineated by Amberlyst 15 catalyzed condensation of pyrrole and heterocyclic aldehydes (2), not reported earlier. The compounds 3a and 3b have been formylated to 5-[di(5-formyl-1H-pyrrol-2-yl)methyl]-1H-pyrrole-2-carbaldehyde (4a) and 5[(5-formyl-1H-pyrrol-2-yl)(3-pyridinyl)methyl]-1H-pyrrole-...
متن کاملSynthesis of Calix[4]pyrrolidine, Calix[m]tetrahydrofuran[n]pyrrolidine (m+n=4) and Similar Macrocyclic Systems - Elucidation of the Hydrogenation Sequence and Factors Influencing the Stereoselectivity
he first meso-octaalkylporphyrinogen (calix[4]pyrrole) was synthesized by Baeyer more than 120 years ago, mixing pyrrole and acetone in the presence of an acid. 92 First proposed by Chelintzev et al., the correct structure was definitively proven by Rothemund in 1955, 93, 94 followed forty years later by the X-ray analysis. 95 This macrocycle could be obtained in gram scale and in very good yie...
متن کاملCreated Using the Rsc Communication Template (ver. 2.1) - See Www.rsc.org/electronicfiles for Details
Calix[4]pyrroles such as meso-octamethylcalix[4]pyrrole 1 have been extensively studied as anion and ion-pair receptors over recent years. Subsequently ‘strapped’ calix[4]pyrroles, pioneered by Lee and Sessler, have been synthesised that contain a single linker between distal meso-positions. These compounds have increased 15 affinity for anions relative to the parent macrocycle. Recently there ...
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ورودعنوان ژورنال:
- Molecules
دوره 12 11 شماره
صفحات -
تاریخ انتشار 2007