2016
DOI: 10.1002/ejoc.201600351
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A One‐Pot Access to Benzo[b][1,4]selenazines from 2‐Aminoaryl Diselenides

Abstract: Different 2-sulfonylaminoaryl diselenides substituted with electron-withdrawing or -donating groups are transformed in one pot into benzo [b][1,4]selenazines. The reaction uses a substoichiometric amount of Cu(OTf ) 2 , and the mechanism involves a base-mediated 1,4-elimination at selenium with the generation of an o-iminoselenoquinone and a 2-sulfonyl-

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Cited by 25 publications
(9 citation statements)
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“…Organo-chalcogenide scaffolds are topics of intense research in many fields of medicinal chemistry in the last decades. [1][2][3] Selenium and sulfur have been demonstrated to play an important role in biological systems as part of the active site in many proteins 4,5 and their organo-derivatives can be employed as antioxidant 6 , antimicrobial 7 , and antitumor agents. 8 These therapeutic agents also act as modulators on a variety of enzyme such as nitric oxide synthase (NOS), 9 inosine monophosphate dehydrogenase (IMDPH) 10 , lipoxygenases (LOX) 11 and more recently, as carbonic anhydrase (CA, E.C.…”
Section: Introductionmentioning
confidence: 99%
“…Organo-chalcogenide scaffolds are topics of intense research in many fields of medicinal chemistry in the last decades. [1][2][3] Selenium and sulfur have been demonstrated to play an important role in biological systems as part of the active site in many proteins 4,5 and their organo-derivatives can be employed as antioxidant 6 , antimicrobial 7 , and antitumor agents. 8 These therapeutic agents also act as modulators on a variety of enzyme such as nitric oxide synthase (NOS), 9 inosine monophosphate dehydrogenase (IMDPH) 10 , lipoxygenases (LOX) 11 and more recently, as carbonic anhydrase (CA, E.C.…”
Section: Introductionmentioning
confidence: 99%
“…The bis- o -nitrobenzene diselenides were initially prepared through the nucleophilic aromatic substitution of o -halonitrobenzenes with K 2 Se 2 (generated in situ) from a modified simple methodology [ 51 ]. After this, we carried out the reduction of bis- o -nitrobenzene diselenides from a well-established procedure described in the literature [ 52 ] using low-cost iron sulfate heptahydrate (FeSO 4 .7H 2 O) to synthesize the aniline-derived diselenides ( Scheme 1 ).…”
Section: Resultsmentioning
confidence: 99%
“…111 In . 134 Recently, the selenocyclization approach was applied by Wang and Bates for the synthesis of one intermediate during the total synthesis of natural product allahabadolactone A. 135 Scheme 22.…”
Section: Selenocyclizationsmentioning
confidence: 99%