Efficient One-Pot Synthesis of Naphthoquinone-Fused Phosphorous Heterocycles via Mannich-Type Reaction

A series of naphthoquinone-fused phosphorus heterocycles was synthesized via a three-component Mannich-type reaction. 2-Chloroethoxylphosphorodichloridite was used as a phosphorus substrate to explore the structure–activity relationships of the 2-position of the heterocycles. One spiral heterocycle compound was structurally characterized by a single-crystal X-ray diffraction analysis.

[1]  J. Lazo,et al.  Bioactivities of simplified adociaquinone B and naphthoquinone derivatives against Cdc25B, MKP-1, and MKP-3 phosphatases. , 2009, Bioorganic & medicinal chemistry.

[2]  E. Novellino,et al.  A practical, green, and selective approach toward the synthesis of pharmacologically important quinone-containing heterocyclic systems using alumina-catalyzed Michael addition reaction , 2008 .

[3]  Baifan Wang,et al.  Synthesis and biological evaluation of novel naphthoquinone fused cyclic aminoalkylphosphonates and aminoalkylphosphonic monoester , 2008, Amino Acids.

[4]  Zhiwei Miao,et al.  A simple and convenient procedure for the synthesis of naphthoquinone fused cyclic α-aminophosphoryl chloride , 2007 .

[5]  M. Roberti,et al.  Nitrogen-containing heterocyclic quinones: a class of potential selective antitumor agents. , 2007, Mini reviews in medicinal chemistry.

[6]  J. Reiner,et al.  Synthesis of novel substituted naphthoquino[b]-benzo[e][1,4]diazepines via Pictet-Spengler cyclization , 2007 .

[7]  You Huang,et al.  A convenient synthesis of 2-alkoxy-2-oxo-1,4,2-oxazaphosphinanes , 2007 .

[8]  Y. Huang,et al.  Synthesis of Novel Naphthoquinone Fused Cyclic a-Aminophosphonates , 2006 .

[9]  Kazuhiro Kobayashi,et al.  Synthesis of Benzo[2,1-b:3,4-b']dithiophene-4,5-dione Derivatives , 2006 .

[10]  B. Ducommun,et al.  Synthesis and biological evaluation of novel heterocyclic quinones as inhibitors of the dual specificity protein phosphatase CDC25C. , 2006, Bioorganic & medicinal chemistry letters.

[11]  A. Dandia,et al.  Multistep Microwave Assisted Solvent Free Green Chemical Synthesis of 2,7-Dihydro-3H-Pyridazino[3′,4′:4,5]Indolo[3,2-c]Quinoline-3,13(12H)-Dione , 2006 .

[12]  S. Bittner,et al.  Novel 2-amino-3-(2,4-dinitrophenylamino) derivatives of 1,4-naphthoquinone , 2005 .

[13]  A. Katritzky,et al.  Heterocycles , 2022, Pharmaceutical Chemistry Journal.

[14]  F. Mongin,et al.  Metallation of pyridines and quinolines in the presence of a remote carboxylate group. New syntheses of heterocyclic quinones. , 2004, Organic & biomolecular chemistry.

[15]  B. Ranu,et al.  A simple and green procedure for the synthesis of α-aminophosphonate by a one-pot three-component condensation of carbonyl compound, amine and diethyl phosphite without solvent and catalyst , 2002 .

[16]  Xin Chen,et al.  Cellular pharmacology studies of shikonin derivatives , 2002, Phytotherapy research : PTR.

[17]  I. D. Ivanchikova,et al.  An unknown route of cyclocondensation of peri-acetylenylquinones with hydrazine , 2000 .

[18]  Jia Zhou,et al.  Studies on Cyclic α-Aminoalkanephosphonate Compounds: A Novel Synthesis of 2-Phenyl-1,4,2-Benzoxaza (or diaza)phosphorin 2-Oxides , 1999 .

[19]  A. Oliveira,et al.  Electrochemical Properties of Biologically Active Heterocyclic Naphthoquinones , 1998 .

[20]  B. Walker,et al.  A highly convenient route to optically pure α-aminophosphonic acids , 1995 .

[21]  C. Yuan,et al.  Studies on Organophosphorus Compounds; XLI. A Convenient Synthesis of Alkyl Hydrogen α-(Benzyloxycarbonylamino)benzylphosphonates , 1990 .

[22]  陈寿军,et al.  Studies on organophosphours compounds XLVI: a facile and direct route to dialkyl 1-(benzyl(oxycarbonylamino)alkyl phosphonates and dialkyl or diphenyl - (benzyloxycarbonylamino)benzylphosphonates , 1990 .

[23]  K. Lee,et al.  Antitumor agents. 89. Psychorubrin, a new cytotoxic naphthoquinone from Psychotria rubra and its structure-activity relationships. , 1987, Journal of medicinal chemistry.

[24]  B. Weiss,et al.  Endonuclease IV of Escherichia coli is induced by paraquat. , 1987, Proceedings of the National Academy of Sciences of the United States of America.

[25]  I. Fridovich,et al.  alpha, beta-Dihydroxyisovalerate dehydratase. A superoxide-sensitive enzyme. , 1987, The Journal of biological chemistry.

[26]  C. Yuan,et al.  Studies on organophosphorus compounds. XX: A facile synthesis of α-amino-substituted benzylphosphonic and -phosphinic acids by use of thiophosphoramide , 1986 .

[27]  I. Fridovich,et al.  Manganese and Defenses against Oxygen Toxicity in Lactobacillus plantarum , 1981, Journal of bacteriology.

[28]  F. Vogel,et al.  The toxicity of melanin precursors. , 1978, The Journal of investigative dermatology.

[29]  G. H. Birum Urylenediphosphonates. General method for the synthesis of .alpha.-ureidophosphonates and related structures , 1974 .

[30]  R. Irani,et al.  The Direct Synthesis of α-Aminomethylphosphonic Acids. Mannich-Type Reactions with Orthophosphorous Acid , 1966 .

[31]  D. R. Martin,et al.  Fluorination of Methoxydichlorophosphine1 , 1950 .

[32]  H D Dakin,et al.  On Amino-acids. , 1918, The Biochemical journal.