One-Pot Synthesis of 2,3-Disubstituted Naphtho[2,3-b]thiophene-4,9-diones from a 2-Sulfenyl-1,4-naphthoquinone and Enamines

The title naphthothiophenequinone derivatives were generally synthesized in one-pot using a tandem conjugate addition–cyclization sequence between 2-[2-(ethoxycarbonyl)ethyl]thio-1,4-naphthoquinone and enamines, derived from cyclic and acyclic ketones.

[1]  Kazuhiro Kobayashi,et al.  One-pot preparation of 1H-naphtho[2,3-c]pyran-5,10-diones and its application to concise total synthesis of (±)-eleutherin and (±)-isoeleutherin , 1998 .

[2]  K. Maeda,et al.  A Direct One-Pot Preparation of Naphtho[2,3-b]furan-4,9-diones from 2-Hydroxy-1,4-naphthoquinones and Enamines , 1998 .

[3]  Masako Mori,et al.  One-Step Synthesis of Naphthofurandione, Benzofurandione, and Phenalenofuranone Derivatives by the CAN-Mediated Cycloaddition , 1998 .

[4]  Kazuhiro Kobayashi,et al.  One-pot synthesis of naphtho[2,3-b]furan-4,9-diones by sequential coupling/ring closure reactions , 1997 .

[5]  Che-Ping Chuang,et al.  Oxidative free radical reaction of 2-phenylthio-1,4-naphthoquinones initiated by manganese(III) acetate , 1996 .

[6]  A. Loupy,et al.  Microwave assisted synthesis of heterocyclic fused quinones in dry media , 1995 .

[7]  M. Brimble,et al.  Formal synthesis of the juglomycins , 1994 .

[8]  H. Suginome,et al.  One-step synthesis of 2,3-dihydronaphtho[2,3-b]thiophene-4,9-diones by a new regioselective [3 + 2] photoaddition of photogenerated 2-mercapto-1,4-naphthoquinone with alkenes , 1993 .

[9]  J. Pingarrón,et al.  Novel .pi.-extended thiophene-fused electron acceptors for organic metals , 1992 .

[10]  M. Hanack,et al.  Synthese, electrochemical properties and crystal structure of tetracyano-p-quinodimethane (TCNQ) derivatives with π-extended systems containing a sulfur atom , 1992 .

[11]  M. Brimble,et al.  The synthesis of 5′-deoxyjuglomycin A and 5′-methoxyjuglomycin A. , 1991 .

[12]  Takayuki Okatani,et al.  Studies on inhibitors of skin tumor promotion, VI. Inhibitory effects of quinones on Epstein-Barr virus activation. , 1989, Journal of natural products.

[13]  V. Snieckus,et al.  Tandem directed metalation reactions. Short syntheses of polycyclic aromatic hydrocarbons and ellipticine alkaloids , 1980 .

[14]  H. Tagawa,et al.  Nonsteroidal Antiinflammatory Agents. III. Syntheses of Benzothienothiepin, Benzothienoxepin and Their Acetic Acid Derivatives , 1978 .

[15]  M. Tateishi,et al.  Synthesis of tanshinones , 1971 .

[16]  M. Tateishi,et al.  Synthesis of Furonaphthoquinones , 1970 .

[17]  H. Kakisawa,et al.  Diels-alder reaction of 3-methylbenzofuran-4,7-quinone II. A revised structure of maturinone , 1969 .

[18]  R. Terrell,et al.  The Enamine Alkylation and Acylation of Carbonyl Compounds , 1963 .

[19]  V. Weinmayr o-(2-Thenoyl)-benzoic Acids and Thiophanthraquinones , 1952 .