Adventures in 1,1-Diphenylacetone Dianion Chemistry

Langer, Peter

doi:10.1055/s-0042-1753200

Cited by 5 publications

(1 citation statement)

References 37 publications

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“…Dianions of 1,3-dicarbonyl compounds follow a different regioselectivity as compared to simple monoanions [6][7][8][9][10][11][12]. For example, 2 can be transformed to its dianion 7 by action of two equivalents of LDA or by sequential addition of sodium hydride and n-butyllithium (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Domino reactions of chromones with activated carbonyl compounds

Langer

2024

Beilstein J. Org. Chem.

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Domino reactions of chromones with activated carbonyl compounds, such as dimethyl acetone-1,3-dicarboxylate and 1,3-diphenylacetone, and with 1,3-bis(silyloxy)-1,3-butadienes, electroneutral equivalents of 1,3-dicarbonyl dianions, allow for a convenient synthesis of a great variety of products. The regioselectivity and course of the reaction depends of the substituent located at carbon C3 of the chromone moiety and also on the type of nucleophile employed.

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Section: Introductionmentioning

confidence: 99%

Domino reactions of chromones with activated carbonyl compounds

Langer

2024

Beilstein J. Org. Chem.

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Adventures in the Chemistry of Multicomponent and Domino Reactions

Langer

2024

Eur J Org Chem

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The present personalized account summarizes various cyclization reactions, including multicomponent and domino processes, which are directed towards the synthesis of complex heterocyclic products. Reactions include, for example, various domino Knoevenagel /cyclization reactions, formal [3+3] cyclizations of pyridinium salts and of thioxindoles with fluoroaroyl chlorides, cyclizations of heterocyclic enamines with diimines and triazines, formal [3+3] cyclizations of 2,4,6‐tris(trifluoromethyl)‐1,3,5‐triazine with 1,3‐bis(silyloxy)‐1,3‐butadienes and domino [4+2] / retro [4+2] reactions of 2‐ethynylpyridines with electron‐rich dienes.

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Adventures in CH-Arylation Chemistry

Langer

2024

Synlett

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The present article provides a personalized account on CH-arylation reactions employed for the synthesis of heterocycles. The presence of a nitro group allowed for direct and regioselective CH-arylations of pyrazoles, imidazoles, indoles and a variety of purine analogues. Direct CH-arylations without the presence of an activating nitro-group were employed for inter- and intramolecular reactions of purine derivatives, which allowed for the synthesis of a great variety of polycyclic systems. Domino C–N coupling / hydroamination / CH-activation reactions of diarylacetylenes with anilines allowed for the synthesis of polycondensated N-heterocycles. Products include indolo- and azaindolo[1,2-f]phenanthridines, quinolino[3′,4′:4,5]pyrrolo[1,2-f]phenanthridines, pyrimido[5′,4′:4,5]pyrrolo[1,2-f]phenanthridines, and benzothieno[2′,3′:4,5]pyrrolo[1,2-f]phenanthridines. The reaction of N-heterocycles, such as indoles, with 1,1-difluoroalkenes resulted in a twofold addition-elimination reaction to give 1,1-diaminoalkenes, which were transformed by CH-arylation into various polycondensated heterocycles, such as indoloisoquinolines, thienoindolizines, oxepines and helicenes. Pyridofluoranthenes, diindenopyrene and azadiindenopyrenes were prepared by a combination of Pd-catalyzed cross-coupling reactions with acid-mediated cycloisomerizations and Pd-catalyzed intramolecular CH-arylations. Bis(carbazoles), benzodithiazoles, benzodithiophenes and 2,5-diarylpyrroles were prepared by inter- and intramolecular CH-arylation reactions.

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Adventures in 1,1-Diphenylacetone Dianion Chemistry

Cited by 5 publications

References 37 publications

Domino reactions of chromones with activated carbonyl compounds

Domino reactions of chromones with activated carbonyl compounds

Adventures in the Chemistry of Multicomponent and Domino Reactions

Adventures in CH-Arylation Chemistry

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