The preparation and some chemistry of 2,2-dimethyl-1,2-dihydroquinolines

Williamson, Natalie M.; Ward, A. D.

doi:10.1016/j.tet.2004.10.035

Cited by 30 publications

(19 citation statements)

References 17 publications

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“… 18 Attempted synthesis of intermediate 16 by trifluoroacetylation of the corresponding nitroarene as in Scheme 1 failed, presumably due to a combination of steric hindrance and electronic deactivation. 19 We therefore synthesized the Boc-protected compound 14 , 20 which suffers the same steric hindrance but was anticipated to be less electronically deactivated. Gratifyingly, trifluoroacetylation of this intermediate was successful, 19 and subsequent TFA deprotection readily afforded 16 .…”

Section: Resultsmentioning

confidence: 99%

Aminoluciferins Extend Firefly Luciferase Bioluminescence into the Near-Infrared and Can Be Preferred Substrates over d-Luciferin

2014

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Firefly luciferase adenylates and oxidizes d-luciferin to chemically generate visible light and is widely used for biological assays and imaging. Here we show that both luciferase and luciferin can be reengineered to extend the scope of this light-emitting reaction. d-Luciferin can be replaced by synthetic luciferin analogues that increase near-infrared photon flux >10-fold over that of d-luciferin in live luciferase-expressing cells. Firefly luciferase can be mutated to accept and utilize rigid aminoluciferins with high activity in both live and lysed cells yet exhibit 10 000-fold selectivity over the natural luciferase substrate. These new luciferin analogues thus pave the way to an extended family of bioluminescent reporters.

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Section: Resultsmentioning

confidence: 99%

Aminoluciferins Extend Firefly Luciferase Bioluminescence into the Near-Infrared and Can Be Preferred Substrates over d-Luciferin

2014

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“…Several approaches have been reported for the preparation of racemic or achiral dihydroquinolines 9,25,26. A number of asymmetric syntheses are also known 27.…”

Section: Resultsmentioning

confidence: 99%

“…We have observed that dihydroquinolines unprotected at nitrogen are generally unstable to oxidative conditions, but it is possible to generate racemic epoxides from dihydroquinolines with a trifluoroacetyl protecting group and m ‐CPBA as the oxidant 9. We therefore investigated the incorporation of a number of nitrogen protecting groups (Table 1).…”

Section: Resultsmentioning

confidence: 99%

“…General Procedure for the Formation of 1,2‐Dihydroquinolines: 9,26 The required aniline (1 equiv.) and 3‐chloro‐3‐methyl‐but‐1‐yne (1 equiv.)…”

Section: Methodsmentioning

confidence: 99%

“…Synthesis of racemic or achiral tetrahydroquinolines has been achieved by diverse methodologies 8. The generation of epoxides from various nitrogen‐protected dihydroquinoline substrates has only previously been reported by utilizing m ‐CPBA,9 or by hydrobromination with aqueous N ‐bromosuccinimide (NBS) followed by base‐catalysed elimination 10…”

Section: Introductionmentioning

confidence: 99%

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Enantioselective Epoxidation of Dihydroquinolines by Using Iminium Salt Organocatalysts

2014

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Gold‐Catalyzed Hydroarylation of Alkynes

Muratore

Echavarren

2015

Patai's Chemistry of Functional Groups

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Hydroarylations, also called alkenylations of (hetero)arenes are important transformations in organic chemistry. The recent development of gold‐catalyzed processes to achieve such transformations has added a new tool in the chemist's toolbox. Thus, the hydroarylations of alkynes under gold catalysis are reviewed from a mechanistic and practical point of view. Both intramolecular and the more challenging intermolecular alkenylations are considered and described in a comprehensive account that includes detailed mechanisms as well as supporting theoretical calculations when relevant. This chapter also aims at illustrating the reactivity of internal and external alkynes which may differ in certain cases, as well as the various reactivities encountered with heteroarenes and arenes. The employment of supported gold catalysts to perform this type of transformations is also discussed in the last section of the chapter.

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The preparation and some chemistry of 2,2-dimethyl-1,2-dihydroquinolines

Cited by 30 publications

References 17 publications

Aminoluciferins Extend Firefly Luciferase Bioluminescence into the Near-Infrared and Can Be Preferred Substrates over d-Luciferin

Aminoluciferins Extend Firefly Luciferase Bioluminescence into the Near-Infrared and Can Be Preferred Substrates over d-Luciferin

Enantioselective Epoxidation of Dihydroquinolines by Using Iminium Salt Organocatalysts

Gold‐Catalyzed Hydroarylation of Alkynes

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