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Recent Advances on High-Order Dipolar Annulations of Donor–Acceptor Cyclopropanes/Cyclobutanes

Synthesis, 2023
This short review summarizes the recent impressive developments in the high-order dipolar annulations (HODAs) of donor–acceptor cyclopropanes (DACs) and donor–acceptor cyclobutanes (DABs) to afford medium-sized (hetero)cycles.
Liangliang Yang   +3 more
semanticscholar   +1 more source

Halogenated Donor-Acceptor Cyclopropanes as Donor-Acceptor Cyclopropene Surrogates.

Angewandte Chemie
Herein we report (3+2) cycloaddition reactions of halogenated donor-acceptor cyclopropanes (HDACs) as surrogates for donor-acceptor cyclopropenes.
D. Werz   +3 more
semanticscholar   +1 more source

Photoredox Activation of Donor-Acceptor Cyclopropanes: Distonic Radical Cation Reactivity in [3+2] Cycloaddition Reactions.

Angewandte Chemie
Altering the reactivity model of a molecule can potentially eliminate limitations existing in its current paradigm. When it comes to the activation of Donor-Acceptor Cyclopropanes (DACs), Lewis acids have been the state-of-the-art.
Soumitra Maity   +3 more
semanticscholar   +1 more source

Lewis Acid-Enabled Chemodivergent Cycloadditions of Donor-Acceptor Cyclopropanes with Indoline-2-Thiones.

Journal of Organic Chemistry
Lewis acid-enabled reactions of donor-acceptor cyclopropanes (DACs) with indoline-2-thiones are reported. The reaction exhibits tunable annulation depending on the Lewis acid and the substituent at N1 of the indoline-2-thiones.
Chen-Ying Zhai   +5 more
semanticscholar   +1 more source

Rapid Mechanochemical Ring-Opening and 1,3-Bisfunctionalization of Donor-Acceptor Cyclopropanes: Regioselective C(sp2)-H Alkylation of Coumaran and Chromane.

Journal of Organic Chemistry
Regioselective alkylation of 2,3-dihydrobenzofuran (coumaran) and chromane was accomplished through the ring-opening of donor-acceptor cyclopropanes (DACs) under mechanochemical conditions.
Sumeyye Atis, Ferruh Lafzi, Haydar Kilic
semanticscholar   +1 more source

(3+2) Annulation of Donor-Acceptor Cyclopropanes with Difluoroenoxysilanes: Syntheses of gem-Difluorocyclopentenes via α,α-Difluoroketone Scaffolds.

Journal of Organic Chemistry
Herein, we present an acid- and base-mediated approach for ring opening of donor-acceptor cyclopropanes (DACs) followed by (3+2) annulation, yielding biologically relevant gem-difluorinated cyclopentenes via α,α-difluoroketone scaffolds.
Neeraj Yadav, Prabal Banerjee
semanticscholar   +1 more source

Formal Higher‐Order [8 + 3] Cycloaddition of Azaheptafulvenes with Donor‐Acceptor Cyclopropanes

Annalen der Pharmacie
Cyclohepta[b]pyridine derivatives have attracted significant attention owing to their unique bioactivities. Herein, we describe an efficient method to access various cyclohepta[b]pyridine derivatives through formal higher‐order [8+3] cycloaddition of ...
J. Xi   +8 more
semanticscholar   +1 more source

Sc(OTf)3-Catalyzed (3 + 3) Annulation of Quinoxaline-2(1H)-thiones and Donor-Acceptor Cyclopropanes.

Journal of Organic Chemistry
The Sc(OTf)3-catalyzed (3 + 3) annulation of quinoxaline-2(1H)-thiones and donor-acceptor cyclopropanes was achieved in the presence of DBU under air to give functionalized 2,3-dihydro-4H-thiopyrano[2,3-b]quinoxaline derivatives in moderate to high ...
Quanyu Ma   +4 more
semanticscholar   +1 more source

[3 + 2] Annulation of Donor-Acceptor Cyclopropanes with Ammonium Thiocyanate: Interrupted Cascade Leads to Elusive Iminodihydrothiophene Derivatives.

Journal of Organic Chemistry
A zinc iodide-mediated [3 + 2] cyclization between donor-acceptor cyclopropanes and ammonium thiocyanate has been developed to afford 2-imino-tetrahydrothiophene derivatives under mild conditions.
Soumyadeep Roy Chowdhury   +3 more
semanticscholar   +1 more source

Peri-Annulated Indoles from Donor-Acceptor Cyclopropanes: Synthesis of 5,6-Dihydro-1H-[1,2]diazepino[4,5,6-cd]indoles.

Journal of Organic Chemistry
A method for one-step conversion of (3-formylindol-4-yl)-substituted donor-acceptor cyclopropanes to 5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indoles has been developed.
S. Antropov   +4 more
semanticscholar   +1 more source

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