A Stereoselective Michael—Mannich Annelation Strategy for the Construction of Novel Tetrahydrocarbazoles

Williams, David R.; Bawel, Seth A.; Schaugaard, Richard N.

doi:10.1021/acs.orglett.7b02323

Cited by 7 publications

(3 citation statements)

References 46 publications

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“…The Williams group [5d] found a stereoselective Michael‐Mannich addition strategy for the synthesis of tetrahydrocarbazoles, where 1,3‐dienes acted as activated Michael acceptors. Recently, the Chegondi group [5e] developed two stereoselective cycloadditions of cyclohexadienone‐tethered enones.…”

Section: Nucleophilic C3mentioning

confidence: 99%

Recent Studies of Bifunctionalization of Simple Indoles

Wang

et al. 2021

Asian J Org Chem

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Indole structures are extremely important and widely employed in organic synthesis. This review will focus on direct bifunctionalizations of simple indoles in tandem reactions. Recent studies have been divided into four types by trigger mechanisms: (1) nucleophilic C3; (2) nucleophilic NH for cyclization; (3) reduction; (4) oxidation. Reactions with carbocations, pyridines, alkenes, alkynes, aldehydes, imines, halogenated compounds et al were discussed. We hope this review will promote future research in the use of indoles.

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Section: Nucleophilic C3mentioning

confidence: 99%

Recent Studies of Bifunctionalization of Simple Indoles

Wang

et al. 2021

Asian J Org Chem

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“…It focused on the synthesis and antimicrobial activity of compounds produced by combining two biologically active compounds (NSAIDS and THCZ). THCZ and Carbazole ring scaffolds are present in some alkaloids [2], they have a variety of biological effects such as antiviral (3) , antitumor (4) , antibacterial (5,6) and broad-spectrum antifungal activity [7,8]. NSAIDs are considered as non-antibiotic drugs reported to display antibacterial activity [9], Some NSAIDs such as indomethacin and diclofenac have been shown to have synergistic effect with particular antimicrobial drugs [10].…”

Section: Introductionmentioning

confidence: 99%

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2022

J. Med. Chem. Sci.

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New 6-chloro-1,2,3,4-tetrahydrocarbazole compounds were prepared from the reaction of cyclohexanone with 4-chlorophenylhydrazine. The synthesis of heterocyclic compounds was carried out through the reaction of cyclohexanone with 4-chlorophenylhydrazine, then the produced compound was treated with two NSAIDs (indomethacin, diclofenac) by amide bond formation to form N-substituted THCZ by NSAIDs. The characterization of prepared compounds was identified using the 1 H, 13 C NMR and FT-IR spectroscopies. The antimicrobial activity of the synthesized compounds was tested in vitro to discover a good activity as antifungal and moderate as antibacterial, which was confirmed by the docking study of the compounds.

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“…These dienes undergo regio-and stereocontrolled condensations with indoles to afford complex tetrahydrocarbazoles in a single step via a tandem Michael-Mannich reaction. 9 We sought to extend these studies to intramolecular processes which entailed the oxidation of the primary alcohol of 3 to provide aldehyde 4. To our surprise, the use of one equivalent of IBX reagent in DMSO at room temperature readily produced the substituted 2H-pyran 5 with the recovery of much of the starting alcohol.…”

mentioning

confidence: 99%

IBX Oxidations for the Synthesis of Substituted 2H-Pyrans

Williams¹,

Bawel²,

Haddadpour³

et al. 2021

HETEROCYCLES

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Facile oxidation of highly substituted 3,5-hexadien-1-ols using 3-iodoxybenzoic acid (IBX) in DMSO has resulted in a one-pot preparation of 2,3,4,6-tetrasubstituted 2H-pyrans.Cycloisomerizations of the 1-oxatriene moiety, produced in the oxidation, spontaneously occur via a disrotatory oxa-electrocyclization. The 2H-pyran products of Table 1 features three differentiated carbonyl substituents. In Celebration of Professor Yasuyuki Kita on His 77th BirthdayThe pyran heterocycle is a common structural motif found within pharmaceuticals, agrichemicals, and biologically active natural products. Several reviews have summarized a variety of techniques for the preparation of substituted pyrans. 1 Methods for the synthesis of tetrahydropyrans have been extensivelyexplored, and we have previously described a general strategy using asymmetric S E ' allylation reactions for enantiocontrolled syntheses of substituted tetrahydropyrans 2,3 Similarly, the formation of dihydropyrans has attracted much attention because these structural motifs also appear within naturally-occurring macrolactones of biological interest. 4 While syntheses of tetrahydropyrans and dihydropyrans are often focused on issues of stereochemistry and efficient strategies for regiocontrolled substitutions, the increased unsaturation of 2H-pyrans results in the characterization of notably less stable species. Successful methods toward substituted derivatives of this reactive family of pyrans are generally limited in scope.In this communication, we report an efficient preparation of 2H-pyrans stemming from 3-iodoxybenzoic acid (IBX) oxidations of highly substituted 3,5-hexadien-1-ols with in situ electrocyclization. The formation of 2H-pyrans via the oxa-electrocyclization reaction has been reported by several investigators in the course of studies for natural product synthesis, 5 and a recent review has compiled key strategies for

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A Stereoselective Michael—Mannich Annelation Strategy for the Construction of Novel Tetrahydrocarbazoles

Cited by 7 publications

References 46 publications

Recent Studies of Bifunctionalization of Simple Indoles

Recent Studies of Bifunctionalization of Simple Indoles

Untitled

IBX Oxidations for the Synthesis of Substituted 2H-Pyrans

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