Advances in Heterocyclic Chemistry by Alan R. Katritzky

By Alan R. Katritzky

The definitive serial within the box -- for the reason that 1960. * presents up to date fabric on a quick turning out to be and hugely topical topic region * comprises the newest examine protecting a wide selection of heterocyclic subject matters * Written by means of major experts and designed as a guide for college kids and and educational researchers. summary: The definitive serial within the box -- seeing that 1960. * presents up to date fabric on a quick transforming into and hugely topical topic zone * comprises the most recent learn overlaying a wide selection of heterocyclic themes * Written by means of best experts and designed as a instruction manual for college kids and and educational researchers

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Construction started with the Pd-catalyzed cross-coupling of the bis(trialkyltin)pyridine 143 (Scheme 37) with a bromopyridine to give the bisboronated terpyridine 144. Cou­ pling to the corresponding diiodide 145 generated the macrocycle 146. Notably, this was the first synthesis of an expanded sexipyridine. Expanded phenylacetylene-modified terpyridine-based macrocycles have been reported (03JA6907) along with the X-ray crystal structure of an alkyl-substituted ring. 42 Monica Soler et al. Scheme 37 Newkome et al.

2 Pyrimidine A hexameric macrocycle containing two pyrimidine units has been reported by Kauffmann et al. (75AGE714), where the lone pairs of the pyrimidine ligands are directed toward the periphery of the macrocycle. The macrocycle is aromatic and was synthesized in a two-step reaction (Scheme 46), where 4-(3-bromophenyl)pyrimidine was reacted with (3-bromophenyl) lithium forming 184, followed by a homocoupling in the presence of CuCl2 to afford 185. Examples of cyclic hexamers containing pyrimidine-type ligands have been found in the literature (05JSSC2436), such as with 2-pymoH (2-hydro­ xypyrimidine) or 2-dmpymoH (4,6-dimethyl-2-hydroxypyridine).

Another example of a heterocyclic macromolecule containing six pyr­ idine subunits reported by Miyazaki et al. (02TL7945) was N,N0 ,N00 ,N000 , N0000 ,N00000 -hexamethylazacalix[6](2,6)pyridine 123 (Scheme 31), which exhibited more flexibility than previous examples and possessed the pyridine subunits directed towards the ring cavity, able to coordinate Scheme 29 Hexameric Macrocyclic Architectures in Heterocyclic Chemistry Scheme 30 35 36 Monica Soler et al. Scheme 31 Zn(II) ion. The Pd-catalyzed aryl amination of 2,6-dibromopyridine with 2,6-bis(methylamino)pyridine afforded (10%) the hexameric heterocycle 123.

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