15796-71-1Relevant academic research and scientific papers
Tropolone-terminated oligomeric fluorophores with responsive properties to external environment
Takagi, Koji,Saiki, Kazuhiro,Hayashi, Hirokazu,Ohsawa, Hiroyasu,Matsuoka, Shin-Ichi,Suzuki, Masato
experimental part, p. 236 - 241 (2009/05/30)
Tropolone-terminated oligomeric fluorophores (Tp20P, Tp20PV, and Tp20PE) were prepared by palladium-catalyzed coupling reactions. A phenylene-type Tp20P showed an emission maximum in the blue fluorescent region and the fluorescence quantum yield was relat
Stereo- and regiocontrolled hydroxylation of oxyallyl [4+3] cycloadducts. A concise synthesis of hinokitiol
Lee, Jae Chol,Cho, Sung Yun,Cha, Jin Kun
, p. 7675 - 7678 (2007/10/03)
Stereo- and regioselective hydroxylation of 8-oxabicyclo[3.2.1]oct-6-en-3-ones was achieved by the action of (diacetoxyiodo)benzene in methanolic potassium hydroxide (the Moriarty oxidation). Subsequent double elimination afforded a convenient preparation of substituted tropolones, as exemplified in a three-step synthesis of hinokitiol (1).
The Palladium-Mediated Cross Coupling of Bromotropolones with Organostannanes or Arylboronic Acids: Applications to the Synthesis of Natural Products and Natural Product Analogues
Banwell, Martin G.,Cameron, Jennifer M.,Collis, Maree P.,Crisp, Geoffrey T.,Gable, Robert W.,'et al.
, p. 705 - 728 (2007/10/02)
The bromotropolones (4), (5) and (10) undergo palladium-mediated cross coupling with a wide range of organostannanes to produce alkenyl-, alkyl- and aryl-substituted tropolones.The methodology has been applied to the synthesis of the monoterpenes β-dolabrin (11), β-thujaplicin (12), 4-isopropyl-7-methoxytropolone (13) and β-thujaplicinol (14).Cross coupling of bromotropolones (4), (5) and (10) with various aryltrimethylstannanes or arylboronic acids has permitted the preparation of the bicyclic colchicine analogues (30)-(43) which have been tested for tubulin-binding activity.The X-ray crystal structure of the most active of these systems, compound (38), is reported.
Synthesis and Reactions of 2-Arylhydrazinotropones. II. Synthesis of 5-Aryltropolones and B-Ring-Open Colchicine Analogues via Benzidine Type Rearrangement of 2-(2-Arylhydrazino)tropones
Nozoe, Tetsuo,Takase, Kahei,Yasunami, Masafumi,Ando, Masayoshi,Saito, Hiroaki,et al.
, p. 128 - 142 (2007/10/02)
Treatment of a wide variety of 2-(2-arylhydrazino)tropones with ethanolic acid at 50-80 deg C readily gave the benzidine type rearrangement products, 2-amino-5-(4-aminoaryl)tropones, besides minor amounts of byproducts of various type.The main products were conveniently led to the corresponding 5-aryltropolones.Similarly, 2-(2-arylhydrazino)tropones bearing an isopropyl and isopropenyl group at the 4-position afforded 4-substituted 2-amino-5-(4-aminoaryl)tropones as the main products, which were also led to 4-substituted 5-(4-acetamidoaryl)- and 5-(4-methoxyaryl)tropolones.Structural assignments of these products were made on the basis of 1H NMR and other spectral data as well as of chemical transformations to known 5-phenyltropolone and also to 2-acetamido-8-hydroxy-10,10-dimethylcycloheptinden-7(10H)-one.This synthetic scheme may possibly be utilized for a convenient synthesis of B-ring-open analogues of colchicine.
The Palladium-mediated Cross-coupling of Bromotropolones with Organostannanes; Application to Concise Syntheses of β-Dolabrin, β-Thujaplicin, 7-Methoxy-4-isopropyltropolone, and β-Thujaplicinol
Banwell, Martin G.,Collis, Maree P.,Crisp, Geoffrey T.,Lambert, John N.,Reum, Monica E.,Scoble, Judith A.
, p. 616 - 617 (2007/10/02)
The bromotropolones (1), (2), and (3) cross-couple with organostannanes in the presence of palladium(O) to produce alkyl, alkenyl, or aryl substituted tropolones; the methodology has been applied to the synthesis of the monoterpenes β-dolabrin (4), β-thujaplicin (5), 7-methoxy-4-isopropyltropolone (7), and β-thujaplicinol (8).
A Convenient Synthesis of 5-Aryltropolones via Novel Benzidine Type Rearrangement of 2-(2-Arylhydrazino)tropones
Nozoe, Tetsuo,Takase, Kahei,Saito, Hiroaki,Yamamoto, Hiroshi,Imafuku, Kimiaki
, p. 1577 - 1580 (2007/10/02)
Treatment of a wide variety of 2-(2-arylhydrazino)tropones with ethanolic acid at 50-80 deg C readily gave the benzidine type rearrangement products, i.e. 2-amino-5-(4-aminoaryl)tropones, which in turn were conveniently led to the corresponding 5-aryltropolones that can be utilized for synthesizing B-ring-open analogues of colchicine.
