Three-Dimensional Hydrocarbon Cores Based on Multiply Fused Cyclopentane and Indane Units:  Centropolyindanes

Tribenzotriquinacenes bearing three peripheral or bridgehead urea groups stretched into the 3-D space

“…Although the bridgehead chemistry of the tribenzotriquinacenes has been extensively investigated [1–4 7], the attachment of multifunctional groupings at the convex surface of the TBTQ skeleton has been only scarcely examined [4]. Therefore, we subjected the previously described bridgehead triaminotribenzotriquinacene 12 [4] to the reaction with phenylisocyanate in analogy to the conversion of the peripheral triamines 10 and 11 , and isolated the corresponding C 3 v -symmetrical TBTQ tris-urea 7 in very good yield (Scheme 2).…”

“…In the course of our extended research on polyfunctionalized derivatives of tribenzotriquinacene (TBTQ, 1 ) and some hydrocarbon congeners 2 – 4 , which provide a great variety of convex–concave molecular building blocks [1–7], we focused our attention on the synthesis of TBTQ derivatives 5 – 7 with three urea units located at the molecular periphery (Fig. 1).…”

Reactions of arylacetylenic compounds with arenes in the presence of aluminum halides

“…Thus the results of our study demonstrated the efficiency of aluminum halides, AlBr 3 and AlCl 3 , in electrophilic activation of various acetylenic compounds. These reactions underlay simple preparative procedures for the synthesis of indene derivatives that attract interest as potential biologically active substances [36], components of catalytic complexes for polymerization of alkenes [37], and materials for other important applications [38,39].…”

One‐Pot Synthesis of Fused Tricyclic Heterocycles with Quaternary Carbon Stereocenter by Sequential Pauson–Khand Reaction and Formal [3+3] Cycloaddition

“…[1] Among numerous methods which have been developed, the Pauson-Khand annulation reaction, [2] in which tethered enynes undergo a formal [2+2+1] cycloaddition reaction with carbon monoxide to afford bicyclic cyclopentenones, has been a powerful, reliable and routine transformation for the synthesis of complex polycyclic cyclopentane-containing molecules. [3] Furthermore, in recent years, 2-(alkyn-1-yl)-2-enones have been shown to be very useful, reactive, and versatile building blocks to furnish not only highly substituted heterocycles such as furans [4, 5a] and 4H-pyrans, [5b] but also polyfunctional electron-deficient 1,3-dienes and allenes.…”

“…Solvent was removed in vacuo and the residue was purified by column chromatography on silica gel(hexanes/ethyl acetate = 3:1) to give 4 ga (163.1 mg, overall yield, 68 %) . 1 …”