2011
DOI: 10.1016/j.tet.2010.12.001
|View full text |Cite
|
Sign up to set email alerts
|

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

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
3
1

Citation Types

0
15
0

Year Published

2011
2011
2023
2023

Publication Types

Select...
5
1

Relationship

1
5

Authors

Journals

citations
Cited by 19 publications
(15 citation statements)
references
References 34 publications
0
15
0
Order By: Relevance
“…Finally, from the thioacetal 91 , a deprotonation followed by the addition of dimethylformamide led to compound 92 . Protection of the aldehyde moiety and hydrolysis of the thioacetal group of 93 gave glyoxal derivative 94 which was used to prepare a methoxylated analogue of coelenterazine ( 7 ) 85. A far more complex preparation of an isomer of this glyoxal was also used for the preparation of the 13 C‐labeled methoxylated coelenterazine analogue 86.…”
Section: Synthetic Routes To Coelenterazine and Other Imidazo[12‐mentioning
confidence: 99%
See 2 more Smart Citations
“…Finally, from the thioacetal 91 , a deprotonation followed by the addition of dimethylformamide led to compound 92 . Protection of the aldehyde moiety and hydrolysis of the thioacetal group of 93 gave glyoxal derivative 94 which was used to prepare a methoxylated analogue of coelenterazine ( 7 ) 85. A far more complex preparation of an isomer of this glyoxal was also used for the preparation of the 13 C‐labeled methoxylated coelenterazine analogue 86.…”
Section: Synthetic Routes To Coelenterazine and Other Imidazo[12‐mentioning
confidence: 99%
“…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. From the resulting compound 142 , many Suzuki–Miyaura coupling reaction were achieved, which led to many analogues of coelenterazine 85. 104 Moreover, the preparation of the imidazo[1,2‐ a ]pyrazine 6‐ O ‐triflate 143 could be carried out by a condensation reaction between 142 and the glyoxal 68 .…”
Section: Synthetic Routes To Coelenterazine and Other Imidazo[12‐mentioning
confidence: 99%
See 1 more Smart Citation
“…An organic solution containing TODGA (N,N,N',N'-tetra-n-octyl diglycolamide) (0.2 mol/L) and 5 vol-% 1-octanol in TPH was used as solvent. 31 The TODGA molecule is known to efficiently extract trivalent lanthanides and actinides from moderate to high nitric acid concentrations. 32,33 A weighted amount of the hydrophilic ligand was dissolved in an aqueous NH 4 NO 3 (0.5 mol/L) solution followed by pH adjustment (HNO 3 or NaOH) and addition of traces of 241 Am(III) and 152 Eu(III).…”
Section: Water-soluble Ligandsmentioning
confidence: 99%
“…31 Reaction of 5-O-triflyl-3-benzyl-2-aminopyrazine with different arylboronic acids afforded the coupled products in good yields (Scheme 2.15) showing triflate to be a suitable leaving group. However, the procedure requires a high load (up to 10 mol%) of palladium catalyst.…”
mentioning
confidence: 99%