Three related aromatic [22] heteroporphyrins have been synthesized and characterized, with the target of achieving NIR absorption. The propensity of these smallest π-conjugated macrocycles to absorb in the NIR region is benefitted from the fusion/annelation of the precursor heterocycles.
A cobalt-catalyzed selective remote C-4 alkylation of 8-aminoquinoline amides via C-H activation under irradiation with a CFL lamp in the presence of eosin Y at room temperature has been achieved. A series of pharmaceutically important C-4 quinoline amide-substituted ether derivatives has been obtained by this procedure. The C-4 functionalization of quinoline amides with inert ether is of much significance and was not reported earlier.
Bicyclic arenyl selenides
are of much importance because of their
pharmaceutical applications. A simple method for their synthesis has
been developed by a reaction of 2-naphthol and styrenyl selenocyanate/diaryl
diselenide in the presence of a base at room temperature. The selenation
occurs exclusively at the 1-position of 2-naphthol unit. The reactions
are relatively fast (2–4 h) and high yielding. A library of
substituted naphthyl styrenyl and naphthyl aryl selenides are obtained
by this procedure.
The inert C-H bond functionalization via bond activation in the presence of transition metals using ball milling is reviewed. The use of several transition metals, such as Pd, Rh, Ru, Co, and Ir are covered in this review for a variety of important functionalizations, including halogenation, amidation, alkynylation, and dehydrogenative coupling, among others. These reactions are performed under mild conditions, usually without any solvent, and in relatively short reaction times.
A convenient method has been developed for the synthesis of biarenyl chalcogenides through the interaction of bicyclic arenes and diaryl dichalcogenides on the surface of basic alumina under ball milling without any metal catalyst or solvent. This methodology shows wide substrate scope and is of high potential in organic synthesis due to its green aspects of ease of operation, shorter reaction time, ambient conditions and high yields.
An efficient method for the C(sp) amidation of 8-aminoquinoline benzamide by acyl azide in the presence of copper acetate has been achieved via C-H activation. Interestingly, the loading of copper acetate has a strong influence on the outcome of the reaction. The use of 1 equiv of copper acetate produces the corresponding aroyl amide, whereas the use of 2 equiv led to acetyl amide. A series of substituted benzoyl and acetyl amides has been obtained.
Theb enzoxazine scaffolds are of much interesta st hey are found in al arge array of natural productsa nd pharmaceutical drugsw ith diverse activities.W eh aved eveloped ap alladium-catalyzed decarboxylative selectivem ono-and bis-acylation of 4H-benzo[d][1,3]oxazin-4-oned erivatives with a-oxo carboxylic acids via preferential cyclic imine-N-directed C À Ha ctivation.2 -Aryl-4H-benzo[d] [1,3]oxazin-4-one was acylated with av arietyo fs ubstitutedp henylglyoxylic acids to produce the corresponding products. It was observed that electron-donating groups (CH 3 ,O CH 3 )a ta ny position of the aromatic ring of phenylglyoxylic acid provided good to excellent yields,w hereasp henylglyoxylica cids containing electron-withdrawing groups (COCH 3 ,C N, NO 2 )g avet he productsi nm oderate yields.I nterest-ingly when the reactionw as performed with silver triflate (AgOTf) in place of silver nitrate (AgNO 3 ) in the presence of 4e quivalents of glyoxylic acid, the bis-acylated product was obtained together with as mall amount of mono-acylated product. This is the first report of acylation of 2-aryl-4H-benzo[d] [1,3]oxazin-4-ones via C À Ha ctivation. Then otable featureso ft his reactiona re acylation with more challenging heteroarene-oxo carboxylic acids and alkyl oxo carboxylic acids.T his new protocolp rovides an easy ande fficient access to av ariety of oacyl-4H-benzo[d][1,3]oxazin-4-one derivatives which are of pharmaceutical importance. Figure1.Af ew biologically active molecules containing the 4H-benzo[d][1,3]oxazin-4-onemoiety. Scheme2.C À Ha cylation of benzoxazine-4-ones with heteroarylglyoxylic acids. 286 asc.wiley-vch.de 2 016 Wiley-VCH Verlag GmbH &Co. KGaA, Weinheim Adv.Synth. Catal. 2016, 358,283 -295 FULL PAPERS Biju Majhi et al. Scheme 3. Pd-catalyzedC À Ha cylationo f2 -phenyl-4Hbenzo[d][1,3]oxazin-4-one with alkyl a-oxo carboxylic acids. Scheme 4. C À HAcylation of meta-substituted 2-aryl-4H-benzo[d][1,3]oxazin-4-ones.
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