A Facile Synthesis of 4‐(O,O‐Dialkylphosphoryl)‐1,3‐oxazole by Rhodium‐Catalyzed Heterocycloaddition

Abstract A series of 4‐phosphoryl substituted 1,3‐oxazole are prepared conveniently by reaction of diethyl 1‐diazo‐2‐oxo‐alkylphosphonates and aromatic nitriles in the presence of a catalytic amount of rhodium(II) acetate. #Studies on Organophosphorus Compounds, Part 131. For Part 130, see C. Xu and C. Yuan, Tetrahedron 2004, 60, 3883–389.

[1]  P. Wipf,et al.  FROM AZIRIDINES TO OXAZOLINES AND THIAZOLINES : THE HETEROCYCLIC ROUTE TO THIANGAZOLE , 2004 .

[2]  J. Alonso,et al.  Asymmetric synthesis of 2H-azirines derived from phosphine oxides using solid-supported amines. Ring opening of azirines with carboxylic acids. , 2002, The Journal of organic chemistry.

[3]  Ross A. Miller,et al.  A direct preparation of silyl oxazoles: a dramatic chemoselectivity difference between R3SiOTf and R3SiCl , 2002 .

[4]  J. Lewis Amaryllidaceae, sceletium, imidazole, oxazole, thiazole, peptide and miscellaneous alkaloids. , 2002, Natural product reports.

[5]  D. Schmatz,et al.  Synthesis of nodulisporic acid 2' '-oxazoles and 2' '-thiazoles. , 2001, Organic letters.

[6]  F. Yokokawa,et al.  Total synthesis of (−)-hennoxazole A , 2001 .

[7]  J. Liebscher,et al.  Total synthesis of phorbazole C , 2001 .

[8]  P. Wipf,et al.  Synthetic studies toward diazonamide A. A novel approach for polyoxazole synthesis. , 2001, Organic letters.

[9]  F. Yokokawa,et al.  Total synthesis of the antiviral marine natural product (-)-hennoxazole A. , 2000, Organic letters.

[10]  J. Lewis Amaryllidaceae, muscarine, imidazole, oxazole, thiazole and peptide alkaloids, and other miscellaneous alkaloids. , 2000, Natural product reports.

[11]  P. Wolbers,et al.  Synthesis of the enantiopure C15–C26 segment of phorboxazole A and B , 1999 .

[12]  C. Walsh,et al.  Thiazole and oxazole peptides: biosynthesis and molecular machinery. , 1999, Natural product reports.

[13]  F. W. Hartner 3.04 – Oxazoles , 1996 .

[14]  Alan R. Katritzky,et al.  Comprehensive Heterocyclic Chemistry IV , 1996 .

[15]  Jong Chan Lee,et al.  An Improved and Efficient Method for Diazo Transfer Reaction of Active Methylene Compounds , 1995 .

[16]  R. Shapiro Dimethyl amino[(phenylthio)methyl]malonate: a useful C-3 unit in a mild, direct synthesis of oxazole-4-carboxylates , 1993 .

[17]  P. Molina,et al.  Iminophosphorane-mediated synthesis of oxazole alkaloids: one-step preparation of O-methylhalfordinol and annuloline , 1993 .

[18]  B. Stowasser,et al.  New hybrid transition state analog inhibitors of HIV protease with peripheric C2-symmetry , 1992 .

[19]  Paweł Kafarski,et al.  BIOLOGICAL ACTIVITY OF AMINOPHOSPHONIC ACIDS , 1991 .

[20]  D. Patel,et al.  Preparation of peptidic α-hydroxy phosphonates a new class of transition state analog renin inhibitors , 1990 .

[21]  D. Villemin,et al.  Potassium Fluoride on Alumina: An Easy Preparation of Diazocarbonyl Compounds , 1989 .

[22]  J. Wood,et al.  Renin inhibitors. Synthesis of transition-state analogue inhibitors containing phosphorus acid derivatives at the scissile bond. , 1989, Journal of medicinal chemistry.

[23]  A. Reitz,et al.  The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspects , 1989 .

[24]  R. D. Connell,et al.  Functionalized oxazoles from rhodiumi-catalyzed reaction of dimethyl diazomalonate with nitriles , 1986 .

[25]  C. Hassall,et al.  Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid. , 1986, Journal of medicinal chemistry.

[26]  C. D. Campbell,et al.  1-Aminoalkylphosphonous acids. Part 1. Isosteres of the protein amino acids , 1985 .

[27]  M. Regitz,et al.  Reaktionen CH-aktiver Verbindungen mit Aziden, XXIII Synthese von α-Diazo-phosphonsäureestern , 1968 .