Preparation of 3,4-Dihydro-2,1-benzothiazine 2,2-Dioxide Skeleton from <i>N</i>-Methyl 2-(Aryl)ethanesulfonamides with (Diacetoxyiodo)arenes

Togo, Hideo; Harada, and Yohsuke; Yokoyama, Masataka

doi:10.1021/jo991419e

Cited by 71 publications

(19 citation statements)

References 28 publications

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“…Whereas the Pd-catalyzed reactions are anticipated to proceed via Pd II /Pd IV redox via C–Pd σ-bond formation, the uncatalyzed reactions could involve interactions of the hypervalent iodine reagent with the nitrogen atoms of the purine ring, and proceed via either radical cations 47–49 and/or nitrogen-centered radicals, 50,51 and/or nitrenium ions. 52–63 Extensive investigations with radical traps indicated that a single mechanism could not be ascribed to the uncatalyzed reactions and that overlapping mechanisms could be responsible for the products formed.…”

Section: Pd-catalyzed and Metal-free Intramolecular C–n Bond Formamentioning

confidence: 99%

When nucleoside chemistry met hypervalent iodine reagents

Lakshman

Zajc

2017

Arkivoc

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There has been increasing use of hypervalent iodine reagents in the field of nucleoside chemistry. Applications span: (a) synthesis of nucleoside analogues with sulfur and seleno sugar surrogates, (b) synthesis of unusual carbocyclic and ether ring-containing nucleosides, (c) introduction of sulfur and selenium into pyrimidine bases of nucleosides and analogues, (d) synthesis of isoxazole and isoxazoline ring-containing nucleoside analogues, (e) involvement of purine ring nitrogen atoms for remote C–H bond oxidation, and (f) metal-catalyzed and uncatalyzed synthesis of benzimidazolyl purine nucleoside analogues by intramolecular C–N bond formation. This review offers a perspective on developments involving the use of hypervalent iodine reagents in the field of nucleoside chemistry that have appeared in the literature in the 2003–2017 time frame.

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Section: Pd-catalyzed and Metal-free Intramolecular C–n Bond Formamentioning

confidence: 99%

When nucleoside chemistry met hypervalent iodine reagents

Lakshman

Zajc

2017

Arkivoc

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“…(B) A new preparative method for 3,4-dihydro-2,1-benzothiazine 2,2-dioxides from N-alkyl 2-(aryl)ethanesulfonamides with DIB and iodine under photochemical conditions has been described. 2 (C) The reaction of specifically protected anhydroalditols with DIB and iodine is a mild and selective procedure for the synthesis of chiral 2,7-dioxabicyclo[2. (D) Treatment of aldoximes with activated alkenes in the presence of DIB afforded isoxazolines smoothly in high yields and under very mild conditions.…”

Section: Introductionmentioning

confidence: 99%

(Diacetoxy)iodobenzene

Lu¹

2006

Synlett

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“…Three practical methods for the preparation of 3,4-dihydro-2,1benzothiazine 2,2-dioxide have been reported prior to our previous method using (diacetoxyiodo)benzene (DIB) and iodine. 3 There are the cyclization of 2-(o-aminophenyl)ethanesulfonic acid, 4a the cyclization of N-benzyl Nmethanesulfonyl(o-chloromethyl)aniline, 4b and the cyclization of N-phenylsulfamoylacetic acid and subsequent reduction of the carbonyl group. 4c These three methods required many steps from commercially available compounds, and the yields of the cyclized products were low.…”

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confidence: 99%

Facile Preparation of 3,4-Dihydro-2,1-benzothiazine 2,2-Dioxides and Related Reaction with 1,3-Diiodo-5,5-dimethylhydantoin under Photochemical Conditions

Moroda¹,

Furuyama²,

Togo³

2009

Synlett

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P r e p a r a t i o n o f 3 , 4 -D i h y d r o -2 , 1 -b e n z o t h i a z i n e 2 , 2 -D i o x i d e sAbstract: 3,4-Dihydro-2,1-benzothiazine 2,2-dioxides were easily obtained in good yields by the reaction of N-methyl 2-arylethanesulfonamides with 1,3-diiodo-5,5-dimethylhydantoin (DIH) under irradiation with a tungsten lamp. When N-benzyl 2-phenylethanesulfonamide was treated with DIH under the same conditions, the corresponding N-benzyl 3,4-dihydro-2,1-benzothiazine 2,2-dioxide was obtained in good yield, and the N-benzyl group was easily removed by the treatment with hydrogen in the presence of Pd(OH) 2 . On the other hand, treatment of N-3-arylpropyl trifluoromethanesulfonamides with DIH under irradiation with a tungsten lamp provided corresponding N-trifluoromethanesulfonyl-1,2,3,4-tetrahydroquinolines in good yields.

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Preparation of 3,4-Dihydro-2,1-benzothiazine 2,2-Dioxide Skeleton from N-Methyl 2-(Aryl)ethanesulfonamides with (Diacetoxyiodo)arenes

Cited by 71 publications

References 28 publications

When nucleoside chemistry met hypervalent iodine reagents

When nucleoside chemistry met hypervalent iodine reagents

(Diacetoxy)iodobenzene

Facile Preparation of 3,4-Dihydro-2,1-benzothiazine 2,2-Dioxides and Related Reaction with 1,3-Diiodo-5,5-dimethylhydantoin under Photochemical Conditions

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