Methyl group functionalization of 6-methylazulene

Robinson, Randall E.; Rudolf, K; Koenig, Tamas

doi:10.1021/jo00350a088

Cited by 7 publications

(2 citation statements)

References 4 publications

(9 reference statements)

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“…8 The methyl group of 6-methylazulene can be easily converted to many different functionalized substituents. 9 In addition, other useful synthetic handles were planned to be introduced in the 1-and 3-positions of azulene (Figure 1). The electron-rich five-membered ring of azulene readily reacts with electrophiles at its 1-and 3-positions.…”

Section: ■ Introductionsupporting

confidence: 82%

“…6-Methylazulene ( 3 ) was chosen as a key intermediate for the synthetic route, as it can be synthesized from common and inexpensive starting materials in two steps . The methyl group of 6-methylazulene can be easily converted to many different functionalized substituents . In addition, other useful synthetic handles were planned to be introduced in the 1- and 3-positions of azulene (Figure ).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of 1,3,6-Trisubstituted Azulenes

et al. 2015

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We have developed a short, general synthetic route to 1,3,6-trisubstituted azulenes. The key intermediate, 6-methylazulene, was synthesized from readily available and inexpensive starting materials in 63% yield over two steps. The methyl group of 6-methylazulene was then used as a synthetic handle to introduce different substituents at the 6-position via two different methods. Subsequently, the 1- and 3-positions were substituted with additional functional handles, such as formyl, chloromethylketone, and iodide. The efficiency of the synthetic route was demonstrated by preparing a collection of three different products with the best demonstrated yield 33% over seven steps.

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Section: ■ Introductionsupporting

confidence: 82%

Section: Introductionmentioning

confidence: 99%