2020
DOI: 10.1002/ange.202009175
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Photoinduced Aerobic Iodoarene‐Catalyzed Spirocyclization of N‐Oxy‐amides to N‐Fused Spirolactams**

Abstract: We report that the spirocyclization of N-oxy-amides to N-fused spirolactams can be achieved under photoinduced aerobic conditions, using a dual iodoarene/pyrylium catalytic system. 13 spirolactams were obtained in this manner and control experiments have shown that the reaction does not proceed if either one of the catalyst is omitted or in the absence of light and/or oxygen. INTRODUCTION: Hypervalent iodine(III) compounds have been known for 130 years, 1 yet interest in their reactivity was very modest until … Show more

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Cited by 11 publications
(9 citation statements)
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“…Various synthetic routes affording to symmetrically or asymmetrically in 2,6 positions were already described in the literature according to classical methods such as (i) the cyclocondensation of dienol of 1,3,5-tricarbonyl compounds under mild acidic catalysis ( i.e. , Brønsted acids such as triflic acid or p -toluenesulfonic acid) and , (ii) the cyclization of diynone, or via an original pathway using an isoxazole intermediate . Herein, we chose to implement the strategies involving either a diynone intermediate, as the most explored and documented pathway to form a γ-pyrone ring, or an oxazole intermediate a priori faster and offering good yields.…”
Section: Resultsmentioning
confidence: 99%
“…Various synthetic routes affording to symmetrically or asymmetrically in 2,6 positions were already described in the literature according to classical methods such as (i) the cyclocondensation of dienol of 1,3,5-tricarbonyl compounds under mild acidic catalysis ( i.e. , Brønsted acids such as triflic acid or p -toluenesulfonic acid) and , (ii) the cyclization of diynone, or via an original pathway using an isoxazole intermediate . Herein, we chose to implement the strategies involving either a diynone intermediate, as the most explored and documented pathway to form a γ-pyrone ring, or an oxazole intermediate a priori faster and offering good yields.…”
Section: Resultsmentioning
confidence: 99%
“…Various synthetic routes affording to symmetrically or asymmetrically in 2,6 positions were already described in the literature according to classical methods such as: (i) the cyclocondensation of the dienol of 1,3,5-tricarbonyl compounds under mild acidic catalysis (i.e. Brønsted acids such as triflic acid or p-toluenesulfonic acid), 9,10 (ii) the cyclization of diynone, 11,12,13 or via an original pathway using an isoxazole intermediate. 14 .…”
Section: Synthesis Of 26-g-pyrone Analogue Of Cyclocurcuminmentioning
confidence: 99%
“…Various synthetic routes affording to symmetrically or asymmetrically in 2,6 positions were already described in the literature according to classical methods such as: (i) the cyclocondensation of the dienol of 1,3,5-tricarbonyl compounds under mild acidic catalysis (i.e. Brønsted acids such as triflic acid or p-toluenesulfonic acid), 9,10 (ii) the cyclization of diynone, 11,12,13 or via an original pathway using an isoxazole intermediate. 14 Herein, we chose to implement the strategies involving either a diynone intermediate, as the most explored and documented pathway to form a g-pyrone ring, and the one involving an oxazole intermediate a priori faster and offering good yields.…”
Section: Synthesis Of 26-g-pyrone Analogue Of Cyclocurcuminmentioning
confidence: 99%
“…Chemical shifts are reported in ppm (δ) relative to deuterated solvent residual peaks. For complete assignment of 1 H and 13 C signals, two-dimensional 1 H, 1 H COSY and 1 H,13 C correlation spectra were recorded. The following abbreviations are used to explain the observed multiplicities: s, singlet; d, doublet; dd, doublet of doublets; ddd, doublet of doublets of doublets; t, triplet; td, triplet of doublets; m, multiplet; bs, broad singlet.…”
mentioning
confidence: 99%