Ultrasound assisted one-pot synthesis of benzo-fused indole-4,9-dinones from 1,4-naphthoquinone and α-aminoacetals

Luu, Quang H.; Guerra, Jorge D.; Castañeda, Cecilio M.; Martínez, Manuel A.; Saunders, Jong; Garcia, Benjamin A.; Gonzales, Brenda V.; Aidunuthula, Anushritha R.; Mito, Shizue

doi:10.1016/j.tetlet.2016.04.031

Cited by 15 publications

(10 citation statements)

References 37 publications

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“…Subsequently, the employment of transition metal‐catalyzed ortho ‐ C−H functionalization means on 3 a was carried out in the presence of Pd(OAc) 2 and NEt 3 (Scheme ). Comparing the spectroscopic data of the product with the reported literature, it indicates that a pyrrole derivative 1 H ‐benzoindole‐4,9‐dione ( 4_Et ) was formed . Fascinatingly, a cyclization reaction in fact took place in this reaction.…”

Section: Resultsmentioning

confidence: 99%

Palladium-Catalyzed C-H Functionalization of Amido-Substitued 1,4-Napthoquinone in the Presence of Amines toward the Formation of Pyrroles and Imidazoles

Chen

Hong

2017

ChemistrySelect

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Transition metal‐catalyzed ortho‐ C−H functionalization of amido‐substituted 1,4‐naphthoquinone, 3, in the presence of Pd(OAc)2 and tertiary amines led to the formations of 4 with newly generated pyrrole rings. Similar reactions were carried out with primary amines and yielded 5, having imidazole rings, as well as amination products 6. In the cases of reacting with secondary amines, the route for the formations of 4‐like, rather than 5‐type, products were prevailed. As revealed from the crystal structures of 4_Bu, 6_Bu, 6_Cy, and 4_Cy, cyclization processes indeed took place to form pyrrole and imidazole rings, respectively, which are fused to the former naphthoquinone framework. The crystal structure of 5_Cy shows that it is a product from amination reaction. Similar reaction was carried out using PCy3 as the phosphine source and an unexpected product 7 was obtained. The crystal structure of 7 exhibits that the moiety of PCy3 attaches to the framework of the former naphthoquinone and brings about a new P=C double bond. In addition, the amide fragment of 3 is hydrolyzed and reduced and forms C=N double bond. Here, distinct reactivity of amines from that of phosphines in this type of reactions have been manifested.

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Section: Resultsmentioning

confidence: 99%

Palladium-Catalyzed C-H Functionalization of Amido-Substitued 1,4-Napthoquinone in the Presence of Amines toward the Formation of Pyrroles and Imidazoles

Chen

Hong

2017

ChemistrySelect

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“…Moreover, compounds 34 can be used as good ligands in metal-organic frameworks thanks to the unique properties of the fluorine atoms. The sonochemical one-pot synthesis of benzo[f]indole-4,9-diones 36 from 1,4-naphthoquinone and α-aminoacetals has recently been described in detail by Luu et al 42 (Scheme 29). The authors sought to develop an efficient synthesis for pindolequinones by using the nucleophilicity of aminoquinones and a 1,4-naphthoquinone amination reaction followed by cyclization to the corresponding benzo-fused indolequinones.…”

Section: Scheme 22mentioning

confidence: 99%

Mechanochemical and sonochemical heterocyclizations

Gaudino

Tagliapietra

Mantegna

et al. 2016

Chem Heterocycl Comp

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Heterocycle formation reactions require efficient catalysis and suitable physical activation. Sonochemistry and mechanochemistry can dramatically promote heterocyclizations in heterogeneous conditions using benign solvents and even in solventless conditions by means of ball mills. Besides facilitating quick cyclization, these technologies bring with them safer protocols, cost reduction, energy saving, process intensification, and waste minimization. The aim of this review is to describe a number of relevant synthetic advances in the last two years and to highlight the huge unexploited potential of both sonochemistry and mechanochemistry.

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“…According to a procedure from Luu et al, 30 could also prepared through reductive amination from stochiometric amounts of benzaldehyde (33) and aminoacetaldehyde dimethyl acetal (8). 11 The latter method furnished 30 in 97% isolated yield. Using secondary amine 30 instead of primary amine 8 for the alkylation gave much better results (Scheme 10).…”

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confidence: 99%

“…The residue was distilled under vacuum to afford 30 as a colorless liquid (5.71 g, 29.2 mmol, 77%). Method 2: According to a modified procedure from Luu et al11 . To a solution of aminoacetaldehyde dimethyl acetal (8, 7.91 g, 75.2 mmol) in dry methanol (300 mL), prepared in an oven-dried Schlenk flask under nitrogen atmosphere, was added freshly distilled benzaldehyde (33, 7.60 mL, 75.2 mmol, 1.0 eq.)…”

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confidence: 99%

Six-Step Gram Scale Synthesis of the HIV Integrase Inhibitor Dolutegravir Sodium

Dietz¹,

Lucas²,

Groß³

et al. 2021

Preprint

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A short and practical synthesis for preparing the active pharmaceutical ingredient dolutegravir sodium was investigated. The convergent strategy developed herein starts from 3-(R)-amino-1- butanol and builds up the BC ring system in 76% isolated yield over four steps. Ring A was constructed by a one-pot 1,4-addition to diethyl-(2E/Z)-2-(ethoxymethylidene)-3-oxobutandioate and subsequent MgBr2·OEt2-mediated regioselective cyclization. Amide formation with 2,4- difluorobenzylamine was either performed from the carboxylic acid or through aminolysis of the corresponding ester precursor. Final salt formation afforded dolutegravir sodium in 48–51% isolated yield (HPLC-purity: 99.7–99.9%) over six linear steps.<br>

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Ultrasound assisted one-pot synthesis of benzo-fused indole-4,9-dinones from 1,4-naphthoquinone and α-aminoacetals

Cited by 15 publications

References 37 publications

Palladium-Catalyzed C-H Functionalization of Amido-Substitued 1,4-Napthoquinone in the Presence of Amines toward the Formation of Pyrroles and Imidazoles

Palladium-Catalyzed C-H Functionalization of Amido-Substitued 1,4-Napthoquinone in the Presence of Amines toward the Formation of Pyrroles and Imidazoles

Mechanochemical and sonochemical heterocyclizations

Six-Step Gram Scale Synthesis of the HIV Integrase Inhibitor Dolutegravir Sodium

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