Facile dimerisation of 3-benzylideneindoline-2-thiones

Thompson, A. M.; Boyd, Michal; Denny, William A.

doi:10.1039/p19930001835

Cited by 16 publications

(10 citation statements)

References 6 publications

(3 reference statements)

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“…Contrary to expectations, the only isolated compound was cycloadduct 7 , resulting from the [4+2]‐cycloaddition of two Knoevenagel adducts 6 (Scheme ). Such a reaction has already been described in the literature when indoline‐2‐thione is treated with benzaldehyde 7…”

Section: Resultsmentioning

confidence: 72%

Synthesis of Substituted 1,2,3,4-Tetrahydro-1-thiacarbazole and Spiro[pyrrolidinone-3,3′-indolinones] through a Common Intermediate Obtained by Condensation of Indolin-2-one, (Aryl)aldehydes, and Meldrum's Acid

et al. 2002

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Trimolecular adducts resulting from condensation between indolin‐2‐one (or indoline‐2‐thione), (aryl)aldehydes, and Meldrum’s acid are useful intermediates for the synthesis of either 1,2,3,4‐tetrahydro‐1‐thiacarbazoles or spiro[pyrrolidino‐3,3′‐oxindoles] related to the natural product horsfiline. These latter compounds were obtained in a three‐step procedure characterized by acyl azide formation, Curtius rearrangement, and subsequent thermal spiro cyclization. The relative stereochemistry of the spiro derivatives was determined by comparison of NOESY data and calculated conformational analyses. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

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Section: Resultsmentioning

confidence: 72%

Synthesis of Substituted 1,2,3,4-Tetrahydro-1-thiacarbazole and Spiro[pyrrolidinone-3,3′-indolinones] through a Common Intermediate Obtained by Condensation of Indolin-2-one, (Aryl)aldehydes, and Meldrum's Acid

et al. 2002

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“…3-Benzylideneindoline-2-thiones were prepared according to the literature procedures from the corresponding aromatic aldehydes and indoline-2-thiones through a Knoevenagel condensation reaction …”

Section: Methodsmentioning

confidence: 99%

“…1 H NMR (600 MHz, CDCl 3 ) δ 8.70 (s, 1H), 8.19 (s, 1H), 8.07 (dd, J = 8.5, 2.4 Hz, 1H), 7.89 (dd, J = 12.2, 8.3 Hz, 3H), 7.77 (dd, J = 8.5, 1.7 Hz, 1H), 7.61–7.52 (m, 1H), 7.36 (d, J = 8.2 Hz, 1H), 7.28–7.24 (m, 1H), 7.19 (t, J = 7.6 Hz, 1H), 7.12 (t, J = 7.6 Hz, 1H), 7.01 (d, J = 8.2 Hz, 2H), 6.79 (t, J = 7.6 Hz, 1H), 6.65 (dd, J = 8.8, 1.7 Hz, 1H), 6.58 (d, J = 7.8 Hz, 1H), 6.09 (d, J = 8.0 Hz, 1H), 5.49 (s, 1H), 5.32 (s, 1H). The analytical data were identical in all respects to those previously reported in the literature …”

Section: Methodsmentioning

confidence: 99%

“…13 C{ 1 H} NMR (151 MHz, DMSO-d 6 ) (the major diastereomer) δ 170. 4,169.7,141.7,139.3,135.7,131.7,131.1,129.5,129.0,128.5,128.0,127.8,126.9,121.3,118.8,117.9,112.2,110.6,60.9,53.0,52.9,50.9, m/z: [M + Na] + Calcd for C 28 H 24 ClNO 4 SNa, 528.1007;Found, 528.1014. Dimethyl 5-(4-Bromophenyl)-2-phenyl-5,10-dihydro-2Hthiepino[2,3-b]indole -4,4(3H)-dicarboxylate (3ca).…”

Section: The Journal Of Organic Chemistrymentioning

confidence: 99%

“…Furthermore, 3-benzylideneindoline-2-thiones, which are formed through the condensation of indoline-2-thiones with aldehydes, have emerged as another potential candidate for synthesizing the indole scaffold (Scheme ). However, 3-benzylideneindoline-2-thiones are unstable compounds and exist in the form of dimers . Therefore, the cycloaddition with other dienophiles poses a unique challenge.…”

Section: Introductionmentioning

confidence: 99%

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Yb(OTf)₃-Catalyzed Formal (4 + 3) Cycloaddition Reactions of 3-Benzylideneindoline-2-thiones with Donor–Acceptor Cyclopropanes

Jiang,

Ma,

Wang

et al. 2023

J. Org. Chem.

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A Yb(OTf)3-catalyzed formal (4 + 3) cycloaddition reaction of donor–acceptor cyclopropanes with 3-benzylideneindoline-2-thiones as sulfur-containing 4π components has been successfully achieved. A series of functionalized 5,10-dihydro-2H-thiepino[2,3-b]indole derivatives were synthesized with good yields and moderate to good diastereoselectivity. The reaction described herein represented the inaugural (4 + 3) cycloaddition of 3-benzylideneindoline-2-thiones.

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Switching between the [2π+2σ] and Hetero‐[4π+2σ] Cycloaddition Reactivity of Bicyclobutanes with Lewis Acid Catalysts Enables the Synthesis of Spirocycles and Bridged Heterocycles

Wang,

Tang,

Xiao

et al. 2024

Angewandte Chemie

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The exploration of the complex chemical diversity of bicyclo[n.1.1]alkanes and their use as benzene bioisosteres has garnered significant attention over the past two decades. Regiodivergent syntheses of thiabicyclo[4.1.1]octanes (S‐BCOs) and highly substituted bicyclo[2.1.1]hexanes (BCHs) using a Lewis acid‐catalyzed formal cycloaddition of bicyclobutanes (BCBs) and 3‐benzylideneindoline‐2‐thione derivatives have been established. The first hetero‐(4+3) cycloaddition of BCBs, catalyzed by Zn(OTf)2, was achieved with a broad substrate scope under mild conditions. In contrast, the less electrophilic BCB ester undergoes a Sc(OTf)3‐catalyzed [2π+2σ] reaction with 1,1,2‐trisubstituted alkenes, yielding BCHs with a spirocyclic quaternary carbon center. Control experiments and preliminary theoretical calculations suggest that the diastereoselective [2π+2σ] product formation may involve a concerted cycloaddition between a zwitterionic intermediate and E‐1,1,2‐trisubstituted alkenes. Additionally, the hetero‐(4+3) cycloaddition may involve a concerted nucleophilic ring‐opening mechanism.

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Facile dimerisation of 3-benzylideneindoline-2-thiones

Cited by 16 publications

References 6 publications

Synthesis of Substituted 1,2,3,4-Tetrahydro-1-thiacarbazole and Spiro[pyrrolidinone-3,3′-indolinones] through a Common Intermediate Obtained by Condensation of Indolin-2-one, (Aryl)aldehydes, and Meldrum's Acid

Synthesis of Substituted 1,2,3,4-Tetrahydro-1-thiacarbazole and Spiro[pyrrolidinone-3,3′-indolinones] through a Common Intermediate Obtained by Condensation of Indolin-2-one, (Aryl)aldehydes, and Meldrum's Acid

Yb(OTf)₃-Catalyzed Formal (4 + 3) Cycloaddition Reactions of 3-Benzylideneindoline-2-thiones with Donor–Acceptor Cyclopropanes

Switching between the [2π+2σ] and Hetero‐[4π+2σ] Cycloaddition Reactivity of Bicyclobutanes with Lewis Acid Catalysts Enables the Synthesis of Spirocycles and Bridged Heterocycles

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Facile dimerisation of 3-benzylideneindoline-2-thiones

Cited by 16 publications

References 6 publications

Synthesis of Substituted 1,2,3,4-Tetrahydro-1-thiacarbazole and Spiro[pyrrolidinone-3,3′-indolinones] through a Common Intermediate Obtained by Condensation of Indolin-2-one, (Aryl)aldehydes, and Meldrum's Acid

Synthesis of Substituted 1,2,3,4-Tetrahydro-1-thiacarbazole and Spiro[pyrrolidinone-3,3′-indolinones] through a Common Intermediate Obtained by Condensation of Indolin-2-one, (Aryl)aldehydes, and Meldrum's Acid

Yb(OTf)3-Catalyzed Formal (4 + 3) Cycloaddition Reactions of 3-Benzylideneindoline-2-thiones with Donor–Acceptor Cyclopropanes

Switching between the [2π+2σ] and Hetero‐[4π+2σ] Cycloaddition Reactivity of Bicyclobutanes with Lewis Acid Catalysts Enables the Synthesis of Spirocycles and Bridged Heterocycles

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Yb(OTf)₃-Catalyzed Formal (4 + 3) Cycloaddition Reactions of 3-Benzylideneindoline-2-thiones with Donor–Acceptor Cyclopropanes