Synthesis of 2-[2-(Ethoxymethoxy)phenyl]spiro[cyclopropane-1,2′-indene]-1′,3′-dione

An 1,3-indanedione-derived donor–acceptor cyclopropane, bearing the ethoxymethyl-protected phenolic group at the ortho-position of the donor aryl substituent, has been synthesized using a reaction sequence involving the Knoevenagel condensation of 1,3-indanedione with the corresponding protected salicylaldehyde followed by the Corey–Chaykovsky cyclopropanation of the obtained adduct with dimethylsulfoxonium methylide. The structure of the synthesized cyclopropane was unambiguously proved by single-crystal X-ray diffraction data.

[1]  R. Unnava,et al.  Synthesis of substituted 1,2-dihydroisoquinolines via Ni(II) and Cu(I)/Ag(I) catalyzed double nucleophilic addition of arylamines to ortho-alkynyl donor-acceptor cyclopropanes (o-ADACs). , 2021, Organic & biomolecular chemistry.

[2]  Yu. V. Tomilov,et al.  GaCl3-Mediated Cascade [2 + 4]-Cycloaddition/[4 + 2]-Annulation of Donor-Acceptor Cyclopropanes with Conjugated Dienes: Strategy for the Construction of Benzobicyclo[3.3.1]nonane Skeleton. , 2021, The Journal of organic chemistry.

[3]  D. Werz,et al.  Exploiting Heavier Organochalcogen Compounds in Donor-Acceptor Cyclopropane Chemistry. , 2021, Accounts of chemical research.

[4]  K. Ghosh,et al.  Recent advances in ring-opening of donor acceptor cyclopropanes using C-nucleophiles. , 2021, Organic & biomolecular chemistry.

[5]  Hua Yang,et al.  Gold/Scandium Bimetallic Catalyzed Formal [5+2]- and [4+2]-Annulations: Access to Tetracyclic Indole Scaffolds , 2021, Chemical Communications.

[6]  Yu. V. Tomilov,et al.  “Diels-Alder reaction” in the ionic version: GaCl3-promoted formation of substituted cyclohexenes from donor–acceptor cyclopropanes and dienes , 2020 .

[7]  J. Waser,et al.  Catalytic Enantioselective Ring-Opening Reactions of Cyclopropanes. , 2020, Chemical reviews.

[8]  Prabal Banerjee,et al.  Donor–Acceptor Cyclopropanes as an Expedient Building Block Towards the Construction of Nitrogen‐Containing Molecules: An Update , 2020 .

[9]  J. Zhao,et al.  Intramolecular Arylative Ring Opening of Donor‐Acceptor Cyclopropanes in the Presence of Triflic Acid: Synthesis of 9 H ‐Fluorenes and 9,10‐Dihydrophenanthrenes , 2019, Asian Journal of Organic Chemistry.

[10]  O. Ivanova,et al.  Donor-Acceptor Cyclopropanes in the Synthesis of Carbocycles. , 2019, Chemical record.

[11]  V. Rybakov,et al.  Synthesis of 2,3-diaryl-2,3,4,4а-tetrahydro-5Н-indeno[1,2-c]pyridazin-5-ones , 2019, Chemistry of Heterocyclic Compounds.

[12]  V. Andronov,et al.  Expanding the Reactivity of Donor-Acceptor Cyclopropanes: Synthesis of Benzannulated Five-Membered Heterocycles via Intramolecular Attack of a Pendant Nucleophilic Group. , 2018, Organic letters.

[13]  M. Melnikov,et al.  Donor-acceptor cyclopropanes as ortho-quinone methide equivalents in formal (4 + 2)-cycloaddition to alkenes. , 2018, Organic & biomolecular chemistry.

[14]  Yu. V. Tomilov,et al.  Methods for the synthesis of donor-acceptor cyclopropanes , 2018 .

[15]  Yu. V. Tomilov,et al.  GaCl3 -Mediated Reactions of Donor-Acceptor Cyclopropanes with Aromatic Aldehydes. , 2016, Angewandte Chemie.

[16]  Yi Pan,et al.  N-Iodosuccinimide-Initiated Spirocyclopropanation of Styrenes with 1,3-Dicarbonyl Compound for the Synthesis of Spirocyclopropanes. , 2016, The Journal of organic chemistry.

[17]  Y. Nelyubina,et al.  Tandem Pd-catalyzed C–C coupling/recyclization of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitro alkanes , 2016 .

[18]  Jun Ren,et al.  Lewis Acid Catalyzed Formal Intramolecular [3 + 3] Cross-Cycloaddition of Cyclopropane 1,1-Diesters for Construction of Benzobicyclo[2.2.2]octane Skeletons. , 2015, Organic letters.

[19]  H. Nambu,et al.  An efficient synthesis of cycloalkane-1,3-dione-2-spirocyclopropanes from 1,3-cycloalkanediones using (1-aryl-2-bromoethyl)-dimethylsulfonium bromides: application to a one-pot synthesis of tetrahydroindol-4(5H)-one , 2015 .

[20]  M. Kerr,et al.  Catalyst-Free Tandem Ring-Opening/Click Reaction of Acetylene-Bearing Donor–Acceptor Cyclopropanes , 2014, Synlett : Accounts and Rapid Communications in Synthetic Organic Chemistry.

[21]  Zifa Shi,et al.  Construction of fused- and spiro-oxa-[n.2.1] skeletons by a tandem epoxide rearrangement/intramolecular [3+2] cycloaddition of cyclopropanes with carbonyls. , 2014, Chemical communications.

[22]  Jun Ren,et al.  Acid-Catalyzed Domino Meinwald Rearrangement of Epoxides/Intramolecular [3+2] Cross-Cycloaddition of Cyclopropane-1,1-dicarboxylates , 2014 .

[23]  D. Werz,et al.  A new golden age for donor-acceptor cyclopropanes. , 2014, Angewandte Chemie.

[24]  Yu. V. Tomilov,et al.  A new type of donor-acceptor cyclopropane reactivity: the generation of formal 1,2- and 1,4-dipoles. , 2014, Angewandte Chemie.

[25]  Zhongwen Wang Polar Intramolecular Cross-Cycloadditions of Cyclopropanes toward Natural Product Synthesis , 2012, Synlett.

[26]  Xue-Yuan Liu,et al.  Lewis acid-catalyzed intramolecular [3+2] cycloaddition of cyclopropane 1,1-diesters with alkynes for the synthesis of cyclopenta[c]chromene skeletons. , 2012, Chemistry, an Asian journal.

[27]  Yu. V. Tomilov,et al.  New dimerization and cascade oligomerization reactions of dimethyl 2-phenylcyclopropan-1,1-dicarboxylate catalyzed by Lewis acids , 2011 .