A unique synthesis of N-(Z)-5-bromo-6-hydroxyhexahydro isobenzofuran-1(3H)-ylidene)methanaminium bromide

Gündoğdu, Özlem; Şahin, Ertan; Kara, Yunus

doi:10.1007/s11696-023-03141-3

Cited by 1 publication

(2 citation statements)

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“…This result makes the applied method even more important (Scheme 3). 21 In this context, considering what kind of product can be obtained by protecting the alcohol group that causes lactone formation, the alcohol group was converted to the corresponding silyl ether with tert-butyldimethylsilyl chloride to give compound 10 (Scheme 4).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Hydrolysis of iminium 8 gave bicyclic lactone 9 (Scheme 2). 21 In light of these findings, we decided to investigate the bromination and epoxidation reactions of cyclohexene derivatives containing N-methyl and N-phenyl-carboxamide units. Here, we report the alternative strategy developed for the synthesis of tetrasubstituted cyclohexane derivatives.…”

Section: ■ Introductionmentioning

confidence: 99%

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Unusual Rearrangements in Cyclohex-3-ene-1-carboxamide Derivatives: Pathway to Bicyclic Lactones

Gundogdu,

Aytaç,

Şahin

et al. 2024

ACS Omega

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The synthesis of new bicyclic lactone derivatives was carried out starting from 2-methyl/phenyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione. 6-(Hydroxymethyl)-N-methyl/phenylcyclohex-3-ene-1-carboxamide derivatives were obtained from the reduction of tetrahydro-1H-isoindole-1,3(2H)-diones with NaBH4. Bromination and epoxidation reactions of both compounds were examined, and the structures of the resulting products were determined by spectroscopic methods. Substituted bicyclic lactone compounds, which are interesting rearrangement products in both bromination and epoxidation reactions, were obtained. In particular, hydroxymethyl (−CH2OH) and amide (−CONHR) groups attached to the cyclohexene ring in the bromination and epoxidation reactions were found to be effective in product formation. As a result, a new and applicable method was developed for the synthesis of bicyclic lactone derivatives.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%