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By Alan R. Katritzky

The definitive serial within the box -- considering 1960. * presents up to date fabric on a quick starting to be and hugely topical topic region * comprises the most recent study overlaying a large choice of heterocyclic issues * Written by way of prime professionals and designed as a instruction manual for college students and and educational researchers. summary: The definitive serial within the box -- when you consider that 1960. * offers updated fabric on a quick starting to be and hugely topical topic quarter * comprises the newest study masking a large choice of heterocyclic issues * Written by means of major professionals and designed as a guide for college students and and educational researchers

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The stepwise procedure for 53 and 54 (Scheme 20) began by reacting 3,5-dibromopyridine and 2-methyl-3-butyn-2­ ol using Sonogashira—Hagihara cross-coupling conditions (75TL4467), fol­ lowed by deprotection to give 3,5-diethynylpyridine (49). Selective coupling with 1-bromo-3-iodobenzene gave the dibromobenzene analog 50, which was then coupled with trimethylsilylacetylene affording 51. Deprotection of the trimethylsilyl groups gave tetrayne 52 that was transformed to either the hexagonal macrocycle 53 using a Sonogashira—Hagihara cross-coupling or 54 via Hay coupling (62JOC3320, 93AGE406).

Schlu¨ter et al. have prepared 2,20 -bipyridine-based macrocycles periph­ erally modified with six hexyloxy groups [as well as others (02EJO3075)] to enhance the ring’s solubility and obtained the X-ray structure (00CEJ2362) and also reported on the macrocycles ruthenium complexa­ tion and X-ray structure determination (02CEJ357). Illustrative of key transformations employed for the construction of these novel materials is the synthesis of macrocycle 127 (Scheme 32) (05EJO822). Beginning with 5,50 -dibromobipyridine, a Suzuki cross-coupling with a hexyloxy­ benzyl arylborate afforded the elongated bipyridine 124 that was then transformed (ICl) to the diiodobipyridine and connected to two equiva­ lents of iodophenylacetylene via another cross-coupling reaction to give the extended diiodide 126.

Mass spectrum detected a peak assigned to the diazakekulene and others assigned to its successive dehydrogenation to afford the fully unsaturated azakekulene 94. The first hexaazakekulene was synthesized (Scheme 27) by Staab et al. (85TL6179), which contained six coplanar nitrogen atoms ideally juxta­ posed for the complexation of small ions. Catalytic hydrogenation of 95 gave 96, which was condensed with benzaldehyde to yield the 2,13­ dibenzylidene derivative 97 and ozonized at —78°C to produce the 32 Monica Soler et al.

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