Intramolecular dipolar cycloaddition reaction of 5H,7H-thiazolo[3,4-c]oxazol-4-ium-1-olates: synthesis of chiral 1H-pyrrolo[1,2-c]thiazole derivatives

Melo, Teresa M. V. D. Pinho e; Barbosa, Dália M.; Ramos, Paulo J. R. S.; Gonsalves, Α. Μ. d’A. Rocha; Gilchrist, T. L.; Beja, Α. Matos; Paixão, J. A.; Silva, Manuela Ramos; Veiga, L. Alte da

doi:10.1039/a807678b

Cited by 18 publications

(13 citation statements)

References 8 publications

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“…These highly strained heterocycles are very useful intermediates in organic synthesis because of their versatile thermal and photochemical behaviour,13,14 as well as their high reactivities toward nucleophilic and electrophilic reagents 15. 2‐Functionalised 2 H ‐azirines are also established as building blocks for the synthesis of a range of heterocyclic compounds 16…”

Section: Resultsmentioning

confidence: 99%

Regio‐ and Stereospecific Cleavage of Stannyloxiranes with Lithium Diphenylphosphide

2009

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Unsubstituted or C‐substituted stannyloxiranes reactedstereospecifically with lithium diphenylphosphide to give either β‐hydroxyphosphane oxides resulting from α‐opening or β‐phosphanyl ketones by β‐opening. Furthermore, the reactivities of distannyloxiranes depend on their configurations. The cis isomers afforded the corresponding α,β‐diphosphanyl alcohols, while the trans isomers were shown to be unreactive. On the other hand, the regiochemistry of the ring‐opening from β‐silyl‐stannyloxiranes is controlled by the tin group and, depending on the nature of the silyl group, led either to stereodefined β‐silylated vinylphosphane oxides or to β‐stannyl silyl enol ethers. Finally, the gem‐silyl‐stannyloxiranes underwent β‐opening to give mixtures of β‐phosphanyl acylsilanes and silyl enol ethers. All compounds are interesting synthons of great versatility in organic chemistry.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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Section: Resultsmentioning

confidence: 99%

Regio‐ and Stereospecific Cleavage of Stannyloxiranes with Lithium Diphenylphosphide

2009

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“…We have been interested in exploring a straightforward approach to new chiral 1 H ,3 H ‐pyrrolo[1,2‐ c ]thiazole derivatives via 1,3‐dipolar cycloaddition of bicyclic münchnones [17–19]. Therefore, we used this synthetic strategy to prepare a range of new chiral 1 H ,3 H ‐pyrrolo[1,2‐ c ]thiazoles retaining the “core quinone” chromophore using 1,4‐naphthoquinones as dipolarophiles.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of new naphthoquinone‐containing pyrrolo‐thiazoles as anticancer agents

Lopes

Laranjo²,

Serra

et al. 2010

Journal of Heterocyclic Chem

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magnified image Naphthoquinones undergo 1,3‐dipolar cycloaddition with bicyclic münchnones generated from thiazolidines affording new pyrrolo‐thiazoles with a fused quinone nucleus. The products were obtained as single enantiomers in good yields. These benzo[f]thiazolo[4,3‐a]isoindole‐6,11(1H,3H)‐diones are comprised of four fused rings and present a very planar structure. The evaluation of their anticancer activity against melanoma A375 and colorectal adenocarcinoma WiDr human cell lines showed only moderate activity but gave insight into the modeling of new structures. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.] J. Heterocyclic Chem., (2010).

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“…We have recently described the use of N-acyl-2-phenyl-(2R,4R)-thiazolidine-4-carboxylic acids to generate 5H,7Hthiazolo [3,4-c]oxazol-4-ium-1-olates with internal dipolarophiles. 1 The intramolecular 1,3-dipolar cycloaddition of these mesoionic species led to the synthesis of new chiral 3,4-dihydro-1H-pyrrolo[1,2-c]thiazole derivatives (1 and 2). The study was now extended to include intermolecular cycloaddition of this type of dipoles.…”

Section: Introductionmentioning

confidence: 99%

Intermolecular Dipolar Cycloaddition Reactions of 5H,7H-Thiazolo[3,4-c]oxazol-4-ium-1-olates

et al. 2000

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Methyl-5-phenyl-5H,7H-thiazolo[3,4-c]oxazol-4-ium-1-olate was generated in the presence of a range of dipolarophiles. The intermolecular 1,3-dipolar cycloaddition of this mesoionic species led to the synthesis of chiral 1H-pyrrolo[1,2-c]thiazole derivatives 7a, 7b, 8, 14, 18, 19 and 20. In the reaction with methyl and ethyl vinyl ketone, spiro compounds 9 and 15 were also obtained. The structure of compound 15 was determined by X-ray crystallography.

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Intramolecular dipolar cycloaddition reaction of 5H,7H-thiazolo[3,4-c]oxazol-4-ium-1-olates: synthesis of chiral 1H-pyrrolo[1,2-c]thiazole derivatives

Cited by 18 publications

References 8 publications

Regio‐ and Stereospecific Cleavage of Stannyloxiranes with Lithium Diphenylphosphide

Regio‐ and Stereospecific Cleavage of Stannyloxiranes with Lithium Diphenylphosphide

Synthesis and biological evaluation of new naphthoquinone‐containing pyrrolo‐thiazoles as anticancer agents

Intermolecular Dipolar Cycloaddition Reactions of 5H,7H-Thiazolo[3,4-c]oxazol-4-ium-1-olates

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