Novel pyrrole C-nucleosides by nitrogen extrusion from pyridazine C-nucleosides

The efficient synthesis of novel polyhydroxy‐tetrahydropyrano‐pyrroles from acetylenic carbohydrate precursors in three to four steps is described. The methodology involves, as key steps, the ring contraction of pyridazine intermediates obtained by an inverse‐demand Diels–Alder reaction and subsequent intramolecular lactonization. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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“…[31] Thus, a similar process was applied to the acetylenic dienophiles 14-(5R), 32, 34, 16α, 21, 26, 27, and 29 (Scheme 4).…”

Section: Access To Pyridazine C-sugarsmentioning

confidence: 99%

Synthesis of Polyhydroxylated Pyrano‐Pyrrole Derivatives from Carbohydrate Precursors

et al. 2007

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“…IR (thin film, cm -1 ) 3031, 2871,1649,1569,1495,1453,1398,1360,1279,1228,1112,1062,879,735,694,625, 592 cm -1 . 1…”

Section: Synthesis Of Nitrone 5 and 10mentioning

confidence: 99%

“…tri-O-benzylaldofuranose (1) (take 1c for example)1 Methanolic solution of H 2 SO 4 was prepared by a careful addition of concentrated H 2 SO 4 (14 mL) to stirred dry MeOH (1800 mL) at 0 ºC. D-ribose (90 g, 0.6 mol) was added slowly.…”

mentioning

confidence: 99%

A Practical Synthesis of Sugar-Derived Cyclic Nitrones: Powerful Synthons for the Synthesis of Iminosugars

Wang¹,

Huang²,

Li³

et al. 2010

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All reagents were used as received from commercial sources without further purification or prepared as described in the literature. Reactions were stirred using Teflon-coated magnetic stirring bars. Analytical TLC was performed with 0.20 mm silica gel 60F plates with 254 nm fluorescent indicator. TLC plates were visualized by ultraviolet light or by treatment with a spray of Pancaldi reagent {(NH 4) 6 MoO 4 , Ce(SO 4) 2 , H 2 SO 4 , H 2 O}. Chromatographic purification of products was carried out by flash column chromatography on silica gel (200-300 mesh). Infrared spectra were recorded on a JASCO FT/IR-480 plus Fourier transform spectrometer. NMR spectra were measured in CDCl 3 (with TMS as internal standard) or D 2 O on a Bruker AV300 (1 H at 300 MHz, 13 C at 75 MHz) or AV600 magnetic resonance spectrometer. Chemical shifts (δ) are reported in ppm, and coupling constants (J) are in Hz. The following abbreviations were used to explain the multiplicities: s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet. Rotation values were recorded on AA10-R polarimeter at the wavelength of sodium D-line (589 nm) at 20°C. Melting points were determined using a FischereJohn melting point apparatus.

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“…[8][9][10][11][12][13][14][15] (B) Recently our group reported the application of 1,2,4,5-tetrazine-3,6-dicarboxylate (1) for the synthesis of pyridazine Cnucleosides 9 from alkynyl C-nucleosides 8. 16 These pyridazines on chemical (Zn/AcOH) or electrochemical 17,18 extrusion of a nitrogen atom afforded novel pyrrole C-nucleosides 10 in good yields. (C) It has been shown by Boger and co-workers that tetrazine 1 reacts with heterodienophiles such as 6 in Diels-Alder reactions to provide 1,2,4-triazines 7.…”

Section: Introductionmentioning

confidence: 99%

Dimethyl 1,2,4,5-Tetrazine-3,6-dicarboxylate

Naud¹

2004

Synlett

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This feature focuses on a reagent chosen by a postgraduate, highlighting the uses and preparation of the reagent in current research Dimethyl 1,2,4,5-Tetrazine-3,6dicarboxylate Compiled by Sébastien Naud Sébastien Naud was born in 1979 in Les Sables d'Olonne, France. He studied chemistry at the University of Nantes where he obtained his Masters. Currently he is doing Ph.D. under the supervision of Prof. Didier Dubreuil in the same university. His area of research includes the synthesis of pyrrole-based cyclic as well as acyclic C-nucleosides from the corresponding pyridazine C-nucleosides by ring contraction.

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Novel pyrrole C-nucleosides by nitrogen extrusion from pyridazine C-nucleosides

Cited by 34 publications

References 9 publications

Synthesis of Polyhydroxylated Pyrano‐Pyrrole Derivatives from Carbohydrate Precursors

Synthesis of Polyhydroxylated Pyrano‐Pyrrole Derivatives from Carbohydrate Precursors

A Practical Synthesis of Sugar-Derived Cyclic Nitrones: Powerful Synthons for the Synthesis of Iminosugars

Dimethyl 1,2,4,5-Tetrazine-3,6-dicarboxylate

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