Facile formation of chiral calixarene analogs incorporating cystine peptide into the macrocyclic ring

Chiral calixarene analogs incorporating cystine peptide into their macrocyclic ring were easily prepared by the cyclization reactions of bis(chloromethyl)phenol-formaldehyde oligomers with cystine peptides in moderate yields. Circular dichroism (CD) spectra indicated the existence of the transmission of the chirality from peptide unit to phenol-formaldehyde oligomer moiety.     

Synthesis of well-defined tower-shaped 1,3,5-trisubstituted adamantanes incorporating a macrocyclic trilactam ring system

We describe the synthesis of two novel well-defined tower-shaped 1,3,5-trisubstituted adamantanes 30 and 33 that incorporate a macrocyclic trilactam ring system. Each nanoscale molecule has a broad tripodal base consisting of three identical sulfur-containing termini as the tripod feet, 4-acetylsulfanylmethylphenyl units in the case of 30 and 3,5-bis(acetylsulfanylmethyl)phenyl units in the case of 33. The sulfur atoms are designed to bind the molecules trivalently to the apex of a gold-coated commercial AFM tip through formation of three S-Au bonds. The rigid adamantane-derived head unit with a single hydrogen atom at the apex is designed to scan the sample. Molecules 30 and 33 are synthesized from 1,3,5-triethynyladamantane by a series of Sonogashira coupling reactions involving terminal alkynes and aryl iodides. A macrocyclic trilactam unit is included for added rigidity. We demonstrate that molecule 30 is sufficiently large and rigid to be visualized by a conventional AFM tip. These nanoscale molecules may also find application as chemically well-defined nanoscale objects for calibration of AFM tips.     

Conformation of thiophene analogs of chalcone containing a naphthalene ring

It has been shown on the basis of dipole moment and IR spectroscopic measurements of thiophene-naphthalene analogs of chalcone that the latter exist in the s-cis form in solutions and have a trans configuration of the substitutents at the double bond and a definite position of the thiophene ring.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1188–1191, September, 1970.     

Synthesis and characterization of naphth-annelated thiophene analogs

Synthesis of symmetrical and unsymmetrical naphth-annelated thienyl heterocycles has been achieved via thionation of hydroxyketones/diketones using Lawesson's reagent. Photophysical studies of 1,3-disubstituted naphtho[c]thiophene analogs are presented. Electro-oxidative behavior of these naphtha-annelated thiophenes are investigated using cyclic voltammeter.     

Synthesis of macrocyclic compounds containing thiophene and thiazole nuclei

Macrocyclic ketones that contain a thiophene nucleus and have 14 or more carbon atoms in the ring can form systems with a condensed thiazole ring, in high yield.Deceased.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 841–844, June, 1986.     

Synthesis and reactions of thiophene analogs of chalcone

A method of synthesizing thiophene analogs of chalcone is described. It is based on condensation of chlorides of , -unsaturated acids with thiophene in the presence of an equimolecular amount of SnCl₄ in benzene or toluene solution. Addition of 2-nitropropane at the active double bond of the thiophene analogs of chalcone gives -nitroketones.     

Synthesis and reactions of thiophene analogs of chalcones

A new method of synthesizing thiophene analogs of chalcones, based on condensing aryl-β-chlorovinyl ketones with thiophene in the presence of stannic chloride, is extended. Hitherto undescribed thiophene analogs of chalcones are obtained in good yields. Addition of 2-nitropropane, nitromethane, and morpholine to the active double bond of thiophene analogs of chalcones gives γ-nitroketones and morpholine derivatives of ketones containing the benzene ring and thiophene. Oxidation with alkaline hydrogen peroxide gives an α-ketooxide of the thiophene analog of chalcone.     

Synthesis and reactions of thiophene analogs of chalcones

A new method of synthesizing thiophene analogs of chalcones, based on condensing aryl--chlorovinyl ketones with thiophene in the presence of stannic chloride, is extended. Hitherto undescribed thiophene analogs of chalcones are obtained in good yields. Addition of 2-nitropropane, nitromethane, and morpholine to the active double bond of thiophene analogs of chalcones gives -nitroketones and morpholine derivatives of ketones containing the benzene ring and thiophene. Oxidation with alkaline hydrogen peroxide gives an -ketooxide of the thiophene analog of chalcone.     

Unsymmetrical squaraines incorporating the thiophene unit for panchromatic dye-sensitized solar cells

Two unsymmetrical squaraines, where the electron-rich 3,4-ethylenedioxythiophene or bithiophene conjugated fragment was used to link unconventionally the squaraine core and the hexyloxyphenyl amino group, were applied for DSCs. The corresponding photovoltaic devices exhibit an attractively panchromatic response and also convert a portion of the near-infrared photons into electricity.     

Synthesis of macrocyclic ligands incorporating sulfur and furan subunits

Abstract

Polyammonium macrocycles containing sulfur and furan units in the macrocyclic ring have been synthesized and studied for ATPase activity. The synthetic methodology involved using tosyl protection for the amines and the formation of macrocyclic Lactams, followed by reduction using borane in THF. Deprotection of the tosylated forms of the macrocycle was accomplished using sodium in butanol for the furan macrocycles, and HBr in HOAc for the sulfur containing macrocycle. The macrocycles were found to be poor catalysts for ATP hydrolysis compared to other similar polyammonium macrocycles.     

Synthesis of chalcone analogs containing a pyrrole ring

Crotonaldehyde-type condensation in alkaline medium of 2-acetylpyrrole or pyrrole-2-aldehyde with aromatic or heterocyclic aldehydes and methyl ketones gives a number of hitherto undescribed pyrrole analogs of chalcone, and their 2, 4-dinitrophenylhydrazones are prepared.     

Synthesis of tricylic systems incorporating the azepine ring

Some tricyclic compounds (derivatives of pyrazino[2,1-a]benzazepine, diazepino[7,1-a]isoquinoline, and some pyrimido[6,1-a]isoquinolines) which are analogs of the anthelmintic praziquantel have been synthesized.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1665–1669, December, 1990.     

Synthesis of macrocyclic ligands containing the indole ring system

2,7-Diformyl-3-methyl-4,6-dimethoxyindole (6) has been synthesized and converted by metal template reactions into the macrocyclic complexes (10–12).