139086-86-5Relevant articles and documents
Template-Assisted Benzannulation Route to Pentacene and Tetracene Derivatives and its Application to Construct Amphiphilic Acenes That Self-Assemble into Helical Wires
Pal, Bikash,Chang, Chun-Hsiung,Zeng, Cian-Jhe,Lin, Chih-Hsiu
, p. 17542 - 17548 (2017)
Pentacene is one of the most versatile organic semiconductors. New synthetic strategies to construct the pentacene skeleton are imperative to produce pentacene derivatives with appropriate solubility, stability, and optoelectronic properties for various applications. This paper describes a template-directed approach to pentacene derivatives. In the retrosynthesis, the acene skeleton is viewed as a laddered double strand polyene instead of the more intuitive linearly fused hexagons. Based on this vision, the template strand of polyene is constructed with Wittig olefination, whereas the second strand is accomplished with Knoevenagel condensation to produce pentacene and tetracene derivatives. The synthetic scheme is flexible enough to generate an array of acene derivatives with substitution patterns that were hitherto difficult to access. Amphiphilic pentacene and tetracene derivatives were also synthesized by the template strategy. One pentacene based amphiphilic rod-coil molecule undergoes self-assembly to form helical wire structures that were visualized with TEM.
A highly regio- and stereoselective cascade annulation of enals and benzodi(enone)s catalyzed by N-heterocyclic carbenes
Fang, Xinqiang,Jiang, Kun,Xing, Chong,Hao, Lin,Chi, Yonggui Robin
supporting information; experimental part, p. 1910 - 1913 (2011/04/16)
Three stereogenic centers in a row: The unconventional activation of enal compounds mediated by an N-heterocyclic carbene (NHC) has generated three consecutive reactive carbon centers that undergo highly regio- and stereoselective annulations with di(enone)s to generate benzotricyclic products containing multiple stereogenic centers (see scheme).
Synthesis of spiro bis-indanes via domino Stetter-aldol-Michael and Stetter-aldol-aldol reactions: Scope and limitations
Sanchez-Larios, Eduardo,Holmes, Janice M.,Daschner, Crystal L.,Gravel, Michel
supporting information; experimental part, p. 1896 - 1904 (2011/08/07)
The synthesis of spiro bis-indanes by means of N-heterocyclic carbene (NHC) catalysis is reported. The dimerization of various o-formylchalcone substrates or their combination with phthaldialdehyde derivatives under the catalysis of thiazolium-derived carbenes afforded Stetter-aldol-Michael products and Stetter-aldol-aldol products, respectively. The use of poor Michael acceptors in conjunction with an N-alkyltriazolium-derived catalyst furnished a variety of dibenzo[8]annulene products. This work highlights the interplay of a variety of factors affecting competing pathways in NHC-catalyzed domino reactions. Georg Thieme Verlag Stuttgart - New York.
First asymmetric synthesis of (Un)saturated 1-Alkylbenzo[c]azepin-3-ones: Extension to the corresponding benzazeplnes
Dumoulin, David,Lebrun, Stepfaane,Deniau, Eric,Couture, Axel,Grandclaudon, Pierre
experimental part, p. 3741 - 3752 (2009/12/05)
A flexible route for the stereoselective synthesis of a variety of structurally diverse (1R)-1-alkyldihydro and tetrahydro-benzazepin(ones) has been developed. The key step is a highly diastereoselective 1,2-addition process applied to a stereopure aromatic hydrazone combined with a ring-closing metathesis reaction to secure the formation of the seven-membered azaheterocycle ring system.
Domino synthesis of bridged bicyclic tetrahydro-1,2-oxazines: Access to stereodefined 4-aminocyclohexanols
Dias, Dwayne A.,Kerr, Michael A.
supporting information; experimental part, p. 3694 - 3697 (2011/03/18)
Image Presented The intramolecular variant of the homo-[3 + 2]-dipolar cycloaddition of nitrones (generated in situ from an aldehyde and a hydroxylamine) with donor-acceptor cyclopropanes allows for the efficient synthesis of bridged tetrahydro-1,2-oxazines. This domino sequence produces adducts amenable to reductive N-O bond cleavage producing cis-1,4- aminocyclohexanols in excellent yields.
Application of the intramolecular isomerisation - Aldolisation from allylic alcohols and allylic silyl ethers to the synthesis of indanones and indenones
Petrignet, Julien,Roisnel, Thierry,Gree, Rene
, p. 7374 - 7384 (2008/03/14)
A new access to indanones was discovered through a one-step nickel or iron-mediated transposition of 2-hydroxyisobenzofurans. Starting from the corresponding silylenol ethers, a new one-pot tandem isomerisation-Mukaiyama aldol process was also developed. These versatile strategies will be useful for the preparation of various types of indanones and indenones.
Asymmetric synthesis of thymine nucleoside analogues based on the isochroman core
Len, Christophe,Violeau, Bruno
, p. 4835 - 4838 (2007/10/03)
Diastereoisomeric analogues of d4T having an isochroman core as the glycone moiety have been prepared in seven steps. Starting from phthalaldehyde, two chiral centres analogous to the α/β anomers of D/L sugars were created. The first was obtained enantiom
Enantiomerical excess determination, purification and biological evaluation of (3S) and (3R) α,β-butenolide analogues of isobenzofuranone
Lipka, Emmanuelle,Vaccher, Marie-Pierre,Vaccher, Claude,Len, Christophe
, p. 501 - 504 (2007/10/03)
The asymmetric synthesis of isobenzofurane analogues, new potential antiviral agents, is reported. High performance liquid chromatography (HPLC) was the technique chosen to separate the enantiomers. We describe this chiral separation and then determine th
1,3-Dihydrobenzo[c]furan nucleoside analogues: Additional studies of the thymine derivative
Egron, David,Perigaud, Christian,Gosselin, Gilles,Aubertin, Anne-Marie,Faraj, Abdesslem,Selouane, Majid,Postel, Denis,Len, Christophe
, p. 4473 - 4475 (2007/10/03)
The detailed study of the 1,3-dihydrobenzo[c]furan derivative of thymine is reported. The lack of anti-HIV activity of this compound in cell culture experiments is shown to be related to the inability of the corresponding 5′-triphosphate derivative to int
Enantiomeric d4T analogues and their structural determination
Selouane, Abdelmajid,Vaccher, Claude,Villa, Pierre,Postel, Denis,Len, Christophe
, p. 407 - 413 (2007/10/03)
Asymmetric synthesis of d4T analogues having a benzo[c]furan moiety with two asymmetric carbon atoms was realized using Sharpless asymmetric dihydroxylation as the key step in a synthesis starting from o-phthalaldehyde. Enantiomeric purities were determin