New PDF release: Advances in Heterocyclic Chemistry

By Alan R. Katritzky

ISBN-10: 0123813069

ISBN-13: 9780123813060

The definitive serial within the box -- seeing that 1960. * offers up to date fabric on a quick transforming into and hugely topical topic quarter * includes the most recent learn masking a wide selection of heterocyclic themes * Written through major specialists and designed as a guide for college students and and educational researchers. summary: The definitive serial within the box -- in view that 1960. * offers up to date fabric on a quick transforming into and hugely topical topic region * comprises the most recent study masking a large choice of heterocyclic subject matters * Written by means of prime experts and designed as a instruction manual for college kids and and educational researchers

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Example text

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. Scheme 26 Scheme 27 Hexameric Macrocyclic Architectures in Heterocyclic Chemistry 33 diketone 98. Reaction with POCl3 in DMF [Vilsmeier reaction (76MI1, 92T3659)] afforded b-chlorovinylaldehyde 99, which when treated with perchloric acid/acetic acids gave dodecahydro-19,20,22,23-tetraaza­ 21,24-dioxoniakekulene (100).

Deprotection using NBS allowed the isolation of the flexible tetraketone macrocycle 76, which was finally converted to the desired sexipyridine 77 by treatment with hydroxylamine in refluxing glacial acetic acid for 24 h. A notable attribute of sexipyridine is the nonplanarity of the connected pyridine rings due presumably to crowding of the adjacent lone N-electron pairs. Calculations suggest a gas-phase lowest energy D3 conformation with ‘up’ and ‘down’ alternating nitrogens (99JCS(P2)2501). Several derivatives of sexipyridine have since been reported.

Starting with the appropriate 1,3-dibromobenzene (Scheme 40), 24 A TMS-acetylene was coupled [Pd(dba)2, CuI, Et3N] to give the diacetylene 155 that was subsequently coupled to terpyridine triflate 156 (91JOC4815) via a Pd(0) cross-coupling procedure to afford the desired elongated bisterpyridine monomer 157. Treatment of the building block 157a with FeCl2, followed by ion exchange with NH4PF6, gave the expanded hexamer 158. A terpyridine-based, Zn(II)-hexamer has been reported (06MMRC1809), whereby an O-hexyl-3,5-bis(terpyridine)phenol ligand was prepared (04OL1197) and subsequently self-assembled.

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Advances in Heterocyclic Chemistry by Alan R. Katritzky


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