Novel synthetic route of aryl-aminopyrazine

Kuse, Masaki; Kondo, Nagako; Ohyabu, Yuki; Isobe, Mitsuaki

doi:10.1016/j.tet.2003.11.052

Cited by 20 publications

(9 citation statements)

References 24 publications

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“…This coupling was first achieved with the N-tosylamide-triflate 8 and 4-methoxyphenylboronate to give aryl aminopyrazine in high yield as reported prevously. 39 Here, we first confirmed that the same SeMcouplings were achievable between the free aminopyrazin-O-triflate 9 and various aryl boronates, such as the thiophyl, naphtyl, biphenyl, 4-phenoxyphenyl, and stylenyl in good yields as shown in Table 1. Incidentally, the aminopyrazinetriflate 9 also showed good reactivity even in the Sonogashira reaction to give the following cross coupling product 13.…”

Section: Pd-mediated Cross Coupling Reactions With Benzylaminopyrazinsupporting

confidence: 69%

“…The necessary triflate 9 was prepared in accordance to our previous paper; thus, 5-pyrazinone 7 was converted to 8 and N-tosyl group was hydrolyzed to amino-benzylpyrazin-O-triflate 9. 39 To this aminopyrazine, a ketoaldehyde equivalent 10 was subjected for condensation to obtain imidazopyrazinone 6-O-triflate 11 (Scheme 3).…”

Section: Preparation Of Imidazopyrazinone 6-o-triflate 11mentioning

confidence: 99%

“…Instead of the fact that R 2 had to be selectively introduced at the early stage of the synthesis, the attempted R 2 introduction at a relatively later stage was achieved to provide two kinds of coelenterazine analogs. 39 The coupling of 5-O-triflyl-3-benzyl-2-aminopyrazine E (X¼OTf) from 4 as a precursor for cross coupling (G from E) at the corresponding position. 39 In this paper, we report more examples of the cross coupling reaction with 2-amino-3-benzyl-5-O-triflate to form five aromatic compounds as summarized in Table 1.…”

Section: Introductionmentioning

confidence: 99%

“…39 The coupling of 5-O-triflyl-3-benzyl-2-aminopyrazine E (X¼OTf) from 4 as a precursor for cross coupling (G from E) at the corresponding position. 39 In this paper, we report more examples of the cross coupling reaction with 2-amino-3-benzyl-5-O-triflate to form five aromatic compounds as summarized in Table 1.…”

Section: Introductionmentioning

confidence: 99%

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Suzuki–Miyaura coupling for general synthesis of dehydrocoelenterazine applicable for 6-position analogs directing toward bioluminescence studies

Phakhodee

Chou

et al. 2011

Tetrahedron

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Section: Pd-mediated Cross Coupling Reactions With Benzylaminopyrazinsupporting

confidence: 69%

Section: Preparation Of Imidazopyrazinone 6-o-triflate 11mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Suzuki–Miyaura coupling for general synthesis of dehydrocoelenterazine applicable for 6-position analogs directing toward bioluminescence studies

Phakhodee

Chou

et al. 2011

Tetrahedron

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“…Finally, from the N ‐protected glycine 134 and the α‐aminonitrile 63 , a 6‐step synthesis allowed the preparation of the 5‐hydroxypyrazine 140 (Scheme ) 103. With this building block, the triflate derivative 141 was made and, prior to a Suzuki–Miyaura reaction, the tosyl protecting group of compound 141 could be hydrolyzed (in concentrated sulfuric acid at 0 °C) without affecting its remarkably stable triflate function 104.…”

Section: Synthetic Routes To Coelenterazine and Other Imidazo[12‐mentioning

confidence: 99%

Synthetic Routes to Coelenterazine and Other Imidazo[1,2‐a]pyrazin‐3‐one Luciferins: Essential Tools for Bioluminescence‐Based Investigations

Coutant

Janin

2015

Chemistry A European J

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In the last few decades, bioluminescent systems based on the expression of a luciferase and the addition of a luciferin to monitor the emission of light have become very important tools for biological investigations. A growing proportion of these systems use coelenterazine or analogues of imidazo[1,2-a]pyrazine luciferins along with photoproteins or luciferases from sea creatures such as Aequorea, Renilla, Gaussia or Oplophorus. Central to the success of these tools are the synthetic pathways developed not only to prepare the naturally occurring luciferins, but also to design altered compounds that exhibit improved bioluminescence. Current work is indeed focused on the design of systems exhibiting extended luminescence ("glow" systems) or redshifted wavelengths, as well as constructions better adapted to conditions in cells or in vivo. This review describes the synthetic pathways used to prepare imidazo[1,2-a]pyrazine luciferins along with the research efforts aimed at preparing analogues even better suited to the design of assays.

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Total Synthesis of (+)‐Cinereain and (−)‐Janoxepin through a Fragment Coupling/Retro‐Claisen Rearrangement Cascade

et al. 2022

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Total syntheses of (+)-cinereain and (À )janoxepin, two fungal cyclotripeptides featuring a complex heterocyclic core and interesting phytotoxic and antimalarial activities, have been achieved in a convergent manner. A key step in this synthesis is a one-pot cascade initiated by the cyclocondensation of two fragments-a hindered 2-vinylcyclopropane-1-acyl fluoride and an electron-deficient cyclic amidine-to release a reactive spiro[2-vinylcyclopropane-1,5'-pyrimidine-4',6'dione]. This intermediate underwent a spontaneous retro-Claisen rearrangement that was rationalized by DFT calculations. The cascade directly afforded a 2,5dihydrooxepin-fused heterotricyclic product, and the challenging oxepin ring was finally forged by the palladium-catalyzed β-hydride elimination of an allylic fluoride intermediate.

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Novel synthetic route of aryl-aminopyrazine

Cited by 20 publications

References 24 publications

Suzuki–Miyaura coupling for general synthesis of dehydrocoelenterazine applicable for 6-position analogs directing toward bioluminescence studies

Suzuki–Miyaura coupling for general synthesis of dehydrocoelenterazine applicable for 6-position analogs directing toward bioluminescence studies

Synthetic Routes to Coelenterazine and Other Imidazo[1,2‐a]pyrazin‐3‐one Luciferins: Essential Tools for Bioluminescence‐Based Investigations

Total Synthesis of (+)‐Cinereain and (−)‐Janoxepin through a Fragment Coupling/Retro‐Claisen Rearrangement Cascade

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