- Synthesis, Rearrangement, and Hauser Annulation of 3-Isocyanophthalides
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3-Isocyanoisobenzofuran-1(3H)-ones (phthalides) were prepared in two steps from the corresponding phthalaldehydic acids. The 3-isocyanoisobenzofuran-1(3H)-ones are readily rearranged to the corresponding 3-cyanoisobenzofuran-1(3H)-ones using triflic anhyd
- Mal, Dipakranjan,Ghosh, Ketaki,Chakraborty, Soumen
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- Studies directed toward total synthesis of rhodocomatulins: A regioselective synthesis of brominated hydroxyanthraquinones by anionic annulations
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In this work, brominated hydroxyanthraquinones, which are the core structural motif of naturally occurring bromorhodocomatulins, were successfully synthesized using Hauser annulation reaction as the key step. When brominated Michael acceptors (brominated p-quinone monoketals) and cyanophthalides or bromocyanophthalides (Hauser donors) were reacted under the annulation conditions, brominated anthraquinones were obtained with 81–87% yields for four examples. On acidic quenching, products were obtained as solid which were separated by filtration and purified by recrystallization in acetone. No chromatography was required.
- Sk, Md Raja,Chakraborty, Soumen,Mal, Dipakranjan
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p. 309 - 317
(2018/02/09)
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- ENEDIYNE COMPOUNDS, CONJUGATES THEREOF, AND USES AND METHODS THEREFOR
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Enediyne compounds having a structure according to formula (I), where R0, R2, R3, R4, R5, R6, and R7 are defined herein, can be used in chemotherapeutic drugs, especially in conjugates, for the treatment of diseases such as cancer.
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Page/Page column
(2013/08/28)
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- Tandem reversible addition-intramolecular lactonization for the synthesis of 3-functionalized phthalides
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A new tandem process based on reversible nucleophilic addition and intramolecular lactonization of methyl 2-formylbenzoate leads to the efficient synthesis of 3-functionalized phthalides, which are important precursors for the synthesis of quinone skeletons via Hauser-Kraus annulation. The reactions are successfully carried out under mild conditions in single operations.
- Sakulsombat, Morakot,Angelin, Marcus,Ramstr?m, Olof
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supporting information; experimental part
p. 75 - 78
(2010/03/01)
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- Total synthesis of the spermidine alkaloid 13-hydroxyisocyclocelabenzine
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A convergent total synthesis of 13-hydroxyisocyclocelabenzine was developed. (3S)-Methyl 3-amino-3-phenylpropanoate (4) was used as the chiral building block. The 3,4-dihydro-4-hydroxyisoquinolin-1(2H)-one derivative (5), the key fragment for the total sy
- Li, Yi,Linden, Anthony,Hesse, Manfred
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p. 579 - 591
(2007/10/03)
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- Efficient synthesis of 4,4-dimethyl-1,9,10(1H)-anthracenetrione
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A concise route to the title compound was achieved via annulation of 4,4-dimethylcyclohexenone with 3-cyanophthalide, followed by oxidation with DDQ.
- Crawley, Matthew L.,Hein, Karl J.,Markgraf, J. Hodge
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p. 470 - 471
(2007/10/03)
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- Cyanidation of halogen compounds and esters catalyzed by PEG400 without solvent
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Primary aliphatic and aromatic nitriles were synthesized in excellent yields (84-96%) and purity by the cyanidation of halogen compounds and esters with dry powdered sodium cyanide catalysed by phase transfer catalyst PEG400 under solvent-free conditions.
- Cao,Chen,Pei
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p. 2203 - 2207
(2007/10/03)
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- AN EFFICIENT SYNTHESIS OF 3-CYANO-1(3H)-ISOBENSOFURANONES
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Reaction of o-formyl-N,N-diethylbenzamides (5) with trimethylsilyl cyanide affords the corresponding (O-trimethylsilyl)cyanohydrins (6), which on treatment with acetic acid produce 3-cyanophthalides (7) in 80-90percent isolated yields.
- Okazaki, Kousuke,Nomura, Keiichi,Yoshii, Eiichi
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p. 1021 - 1028
(2007/10/02)
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- Synthesis of Functionalized Hydroxyphthalides and Their Conversion to 3-Cyano-1(3H)-isobenzofuranones. The Diels-Alder Reaction of Methyl 4,4-Diethoxybutynoate and Cyclohexadienes
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Several methods have been used in the preparation of functionalized hydroxyphthalides.Metalation of N,N-diethyl-3-methoxybenzamide, followed by reaction with dimethylformamide and hydrolysis, furnished 3-hydroxy-4-methoxy-1(3H)-isobenzofuranone in 52perce
- Freskos, John N.,Morrow, Gary W.,Swenton, John S.
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p. 805 - 810
(2007/10/02)
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