Zur Reaktion von 1,2‐Thiazetidin‐1,1‐Dioxiden mit Butyllithium

Meyle, Eberhard; Schwenkkraus, Peter; Zsigmondy, Marion; Otto, Hans‐Hartwig

doi:10.1002/ardp.19893220105

Cited by 16 publications

(2 citation statements)

References 19 publications

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“…An interesting reaction occurred upon attempted lithiation of 17 with nBuLi (Scheme 11). [41] In this case, anions 24 formed upon deprotonation of 17 reacted with the second molecules of the starting materials, resulting in the β-sultam ring-opening and the formation of intermediates 25 (that could be trapped with benzoyl chloride). Further recyclization of 25 gave final products 26.…”

Section: Fused β-Sultamsmentioning

confidence: 99%

Saturated Bicyclic Sultams

et al. 2020

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Saturated bicyclic sultams represent a promising class of sp 3-rich three-dimensional scaffolds of outmost importance to organic and medicinal chemistry. In this review with 99 references, synthesis, properties, and applications of these compounds are surveyed. The literature data are categorized according to the structural types (i.e. fused, bridged, and spirocyclic compounds), as well as homologous series

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Section: Fused β-Sultamsmentioning

confidence: 99%

Saturated Bicyclic Sultams

et al. 2020

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“…Thereby, a deprotonated intermediate is formed [3] that, by reaction with Celectrophiles, yields relatively stable products, as demonstrated by silylation [4], acylation [5], reactions with aromatic nitriles yielding enamino b-sultams [6], and by the rearrangement of 2,3-disubstituted b-sultams into 2,4,1-dithiazine derivatives [7].…”

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confidence: 99%

Properties and Reactions of Substituted 1,2‐Thiazetidine 1,1‐Dioxides: Functionalization and Reactions at C(4) of the β‐Sultam

Plagge

Manicone

Otto

2004

Helvetica Chimica Acta

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The introduction of functional groups at the 4-position of the b-sultam ring was realized by the synthesis of mono-and disubstituted derivatives by reactions of N-silylated b-sultams with electrophiles in the presence of BuLi or LDA. As electrophiles, ketones, chlorosilanes, a b-sultam, CO 2 , chloroformiate, halogen, azodicarboxylate, phenyltriazoledione, tosyl azide, 1,3,5-triazine, propyl nitrate, and phenyl isocyanate were used. Furthermore, a number of derivatives of these substitution products were synthesized. All products were characterized by standard spectroscopic methods, and conformations were studied, supported by calculation.

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Bicyclische β‐Sultame: Darstellung aus monocyclischen β‐Aminothiolen und einige Eigenschaften

Schwenkkraus

Otto

1990

Archiv der Pharmazie

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2-Cyclaminmethanole 3 werden in 2-Cyclaminmethanthiole 7 umgewandelt, aus denen durch oxidative Chlorierung cyclisch substituierte Taurinsiiurechloride 8 zughglich sind. Durch Behandlung mit Basen werden 8 in die bicyclischen p-sdtame 9 ~pekmoskopisck Eigenschaften und solvolysevehalten von 9 werden diskutien Bicyclic p-Sultams: Synthesis from Monocyclic PAminothiols and Some PropertiesThe cyclamine methanethiols 7 are prepared from the corresponding akahols 3 and oxidatively transformed by treatment with chlorine into the cyclic substituted taurinechlorides 8. Upon treatment with bases, 8 is cyclized yielding the bicyclic p-sultams 9. Some spectroscopic properties and the solvolysis of 9 are briefly discussed.

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Zur Reaktion von 1,2‐Thiazetidin‐1,1‐Dioxiden mit Butyllithium

Abstract: 23-Disubstituicrte

Cited by 16 publications

References 19 publications

Saturated Bicyclic Sultams

Saturated Bicyclic Sultams

Properties and Reactions of Substituted 1,2‐Thiazetidine 1,1‐Dioxides: Functionalization and Reactions at C(4) of the β‐Sultam

Bicyclische β‐Sultame: Darstellung aus monocyclischen β‐Aminothiolen und einige Eigenschaften

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