Approach to the blues: A highly flexible route to the azulenes

…, Y Coquerel, M Berthod, AE Greene…

Index: Carret, Sebastien; Blanc, Aurelien; Coquerel, Yoann; Berthod, Mikael; Greene, Andrew E.; Depres, Jean-Pierre Angewandte Chemie - International Edition, 2005 , vol. 44, # 32 p. 5130 - 5133

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Citation Number: 35

Abstract

Scheme 2. Preparation of azulene (1), 4-methylazulene (7), and 1, 4-dimethylazulene (8): a) NaBH4, MeOH/CeCl3, 08C, 1.5 h (from 5a: 96%; from 5b: 98%); b) the Burgess reagent, THF, 0! 208C, 1 h; p-chloranil, 208C, 24 h (from 6a: 47%; from 6b: 52%); c) PMHS, Pd (OAc) 2, dpdb, K3PO4, THF, 808C, 12 h (1: 92%; 7: 91%); d) MeB (OH) 2, Pd (OAc) 2, dpdb, K3PO4, PhMe, 1008C, 24 h (98%). Burgess reagent=(methoxycarbonylsulfamoyl) ...

~89%

~86%

~91%

Synthesis of 1, 1′-, 2, 2′-, 1, 2′-, and 2, 6′-Biazulenes an...

[Morita, Tadayoshi; Takase, Kahei Bulletin of the Chemical Society of Japan, 1982 , vol. 55, # 4 p. 1144 - 1152]

Coupling Reaction of Azulenyl-4, 4, 5, 5-tetramethyl-1, 3, 2...

[Kurotobi, Kei; Tabata, Hiroshi; Miyauchi, Masato; Murafuji, Toshihiro; Sugihara, Yoshikazu Synthesis, 2002 , # 8 p. 1013 - 1016]

Reaction of azulenes with 1-trifluoromethanesulfonylpyridini...

[Ito, Shunji; Yokoyama, Ryuji; Okujima, Tetsuo; Terazono, Tomomi; Kubo, Takahiro; Tajiri, Akio; Watanabe, Masataka; Morita, Noboru Organic and biomolecular chemistry, 2003 , vol. 1, # 11 p. 1947 - 1952]

A short new azulene synthesis

[Scott, Lawrence T.; Minton, Mark A.; Kirms, Mark A. Journal of the American Chemical Society, 1980 , vol. 102, # 20 p. 6311 - 6314]