- One-pot synthesis of fused benzo[c]carbazoles by photochemical intramolecular annulation of 3-acyl-2-haloindoles with tethered styrenes
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An efficient procedure for the synthesis of fused benzo[c]carbazoles has been achieved in moderate to high yields by the one-pot photochemical annulation of 3-acyl-2-haloindoles with tethered styrenes by photoinduced electron-transfer coupling, electrocyclic reactions, and deacylative aromatization in the presence of pyridine. Fused furo[2,3-c]carbazoles were also synthesized under the same conditions. 5,6-Dihydrobenzo[c]pyrrolo[1,2,3-lm] carbazoles were oxidized by DDQ to afford aromatic benzo[c]pyrrolo[1,2,3-lm] carbazole products in moderate to high yields.
- Lu, Shen-Ci,Wei, Shi-Chao,Wang, Wei-Xia,Zhang, Wei,Tu, Zhi-Feng
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supporting information; experimental part
p. 5905 - 5910
(2011/11/06)
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- One-pot synthesis of benzo[f]quinolin-3-ones and benzo[a]phenanthridein-5- ones by the photoanuulation of 6-chloropyridin-2-ones and 3-chloroisoquinolin-1- ones to phenylacetylene
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The one-pot synthesis of benzo[f]quinolin-3-ones and benzo[a] phenanthridein-5-ones was achieved by the inter- and intramolecular photoannulation of 6-chloropyridin-2-ones and 3-chloroisoquinolin-1-ones with phenylacetylene or tethered phenylacetylene. The reactions were proceeded by photoaddition of 6-chloropyridin-2-ones and 3-chloroisoquinolin-1-ones to phenylacetylene to give the chlorine-substituted stilbenoids, and then 6π electrocyclization of the stilbenoids and oxidation aromatization to afford the polycyclic products.
- Wang, Ren,Lu, Shen-Ci,Zhang, Yi-Ming,Shi, Zong-Jun,Zhang, Wei
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supporting information; experimental part
p. 5802 - 5808
(2011/10/02)
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- Nitrite anion: The key intermediate in alkyl nitrates degradative mechanism
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Alkyl nitrates are metabolized in vitro to yield nitric oxide, and thiol groups have long been considered necessary cofactors. Here, we report evidence that no reaction between thiols and alkyl nitrates takes place in vitro, but stronger reducing agents, such as iron(II) derivatives, are necessary; alkoxy radicals and nitrite anions are the reaction intermediates. The latter, in slightly acidic conditions, can nitrosate thiols to the corresponding S-nitrosothiols, the real NO releasers.
- Grossi, Loris
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experimental part
p. 3318 - 3321
(2009/04/05)
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- Synthesis of pyrrolizidines using aminyl radicals generated from sulfenamide precursors
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Tandem radical cyclisations of aminyl radicals generated from sulfenamide precursors have been used for the synthesis of pyrrolizidines and other polycyclic nitrogen heterocycles. The aminyl radicals are generated by reaction between sulfenamide precursor
- Russell Bowman,Clark, David N.,Marmon, Robert J.
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p. 1295 - 1310
(2007/10/02)
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- FORMATION AND REARRANGEMENT OF THE GRIGNARD REAGENT FROM 2-PHENYLCYCLOBUTYLMETHYL BROMIDE
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Reaction of cis- or trans-2-phenylcyclobutylmethyl bromide with magnesium produces the rearranged 5-phenyl-1-penten-5-ylmagnesium compound 7 in addition to the unrearranged Grignard reagent 6.The former appears to result from very rapid rearrangement of a radical intermediate in the process of Grignard reagent formation.Rearrangement of 6 to 7 also occurs, at a rate which is accelerated by the phenyl group.
- Hill, E. Alexander,Harder, Constance L.,Wagner, Richard,Meh, David,Bowman, Richard P.
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