Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 23
43
Views
3
CrossRef citations to date
0
Altmetric
Original Articles

Preparation of 2-[1-Phenyl-1H-pyrazol-5-yl]benzoic Acids from Dilithiated C(α),N-Phenylhydrazones and Methyl Hydrogen Phthalate

, , &
Pages 4150-4159 | Received 20 Nov 2007, Published online: 31 Oct 2008

REFERENCES

  • (a) Watanabe , K. ; Kamuro , Y. ; Taniguchi , E. 2-Phenyl-5H-pyrazolo[5,1-a]isoquinolin-5-ones: Development of new auxin transport inhibitors and their plant growth regulating properties . J. Ag. Food Chem . 1994 , 42 , 2311 – 2316 ; (b) Bures , M. G. ; Black-Schaefer , C. ; Gardner , G. The discovery of novel auxin transport inhibitors by molecular modeling and three-dimensional pattern analysis . J. Computer-Aided Mol. Design 1991 , 5 , 323 – 334 ; (c) Katekar , G. F. ; Geissler , A. E. The distribution of the receptor for 1-N-naphthylphthalamic acid in different tissues of maize . Physiol. Plantarum 1989 , 76 , 183 – 186 ; (d) Katekar , G. F. ; Winkler , D. A. ; Geissler , A. E. A conformational study of the topographical requirements of a phytotropin recognition site on the naphthylphthalamic acid receptor . Phytochem. 1987 , 26 , 2881 – 2889 ; (e) Watanabe , K. ; Taniguchi , E. Syntheses and plant growth-regulating activity of 2-substituted phenylacetic acid derivatives . Ag. Biol. Chem . 1986 , 50 , 2047 – 2052 ; (f) Toja , E. ; Omodei-Sale , A. ; Cattaneo , C. ; Galliani , G. Synthesis and pregnancy terminating activity of 2-arylpyrazolo[5,1-a]isoindoles and -isoquinolines . Eur. J. Med. Chem . 1982 , 17 , 223 – 227 ; (g) Pryor , A. ; Huppatz , J. L. Purification of maize alcohol dehydrogenase and competitive inhibition by pyrazoles . Biochem. Internatnl . 1982 , 4 , 431 – 438 ; (h) Katekar , G. F. ; Nave , J. F. ; Geissler , A. E. Phytotropins, III: Naphthyl-phthalamic acid binding sites on maize coleoptile membranes as possible receptor sites for phytotropin action . Plant Physiol . 1981 , 68 , 1460 – 1464 ; (i) Harris , R. L. N. ; Huppatz , J. L. ; Teitei , T. The effect of C-2-carboxyphenyl derivatives of certain heterocyclic compounds on root geotropism in cress seedlings . Pest. Sci . 1980 , 11 , 439 – 444 ; (j) Johnson , A. L. ; Sweetser , P. B. Pyrazole plant growth regulants . US 3948937, 19760406, 1976 ; Chem. Abstr . 1976 , 85 , 33005 ; (k) Geissler , A. E. ; Huppatz , J. L. ; Katekar , G. F. Effect of substituted pyrazoles and related compounds on geotropism in cress seedlings . Pest. Sci . 1975 , 6 , 441 – 450 ; (l) Johnson , A. L. Cyclization of 2-(3-aryl-5-pyrazolyl) benzoic acids, esters, and amides to 2-arylpyrazolo[5,1-a]-isoindol-8-ones . US 3849436, 19741119, 1974 ; Chem. Abstr . 1975 , 82 , 72989.
  • Johnson , A. L. ; Sweetser , P. B. 2-(3-Aryl-5-pyrazolyl)benzoic acid chemistry . J. Org. Chem . 1976 , 41 , 110 – 114 ; (b) Johnson , A. L. ; Sweetser , P. B. Plant growth regulating 3,5-diphenylpyrazoles . Ger. Offen. DE 2219702, 19721116, 1972 ; Chem. Abstr . 1973 , 78 , 58410.
  • Sedqui , A. ; Lakhlifi , T. ; Vebrel , J. ; Laude , B. Regiochemistry of the reaction of diarylnitrilimines with indenone: Preliminary results . Comptes Rendus de l'Academie des Sciences, Serie II: Mecanique, Physique, Chimie, Sciences de la Terre et de l'Univers 1990 , 310 , 505 – 509.
  • Elguero , J. In Comprehensive Heterocyclic Chemistry ; A. R. Katritzky , C. W. Rees , (Eds.) ; Pergamon Press : New York , 1984 ; vol. 5 , section 4.04 , pp. 167 – 343.
  • Fulmer , T. D. ; Dasher , L. P. ; Bobb , B. L. ; Wilson , J. D. ; Sides , K. L. ; Beam , C. F. An improved synthesis of 3,5-disubstituted isoxazoles and pyrazoles from C(α),O-dilithiooximes and C(α),N-dilithiophenylhydrazones . J. Heterocycl. Chem . 1980 , 17 , 799 – 800 ; (b) Duncan , D. C. ; Trumbo , T. A. ; Almquist , C. D. ; Lentz , T. A. ; Beam , C. F. The preparation of N-carboalkoxypyrazoles and N-phenylpyrazoles from C(α)-dianions of carboalkoxyhydrazones and phenylhydrazones . J. Heterocycl. Chem . 1987 , 24 , 555 – 559 .
  • Huff , A. M. ; Hall , H. L. ; Smith , M. J. ; O'Grady , S. A. ; Waters , F. C. ; Fengl , R. W. ; Welsh , J. A. ; Beam , C. F. The preparation of phenacylpyrazoles, acylpyrazoles, imidazolylisoxazoles, and imidazolylpyrazoles from C(α)-dianions of oximes, phenylhydrazones, and acylhydrazones . J. Heterocycl. Chem . 1985 , 22 , 501 – 504 .
  • Huff , A. M. ; Beam , C. F. The preparation of selected benzopyrano[3,4-b]-pyrazoles by the condensation of C(α),N-dilithiocarboalkoxyhydrazones and salicylate esters . J. Heterocycl. Chem . 1986 , 23 , 1343 – 1346 .
  • Downs , J. R. ; Pastine , S. J. ; Schady , D. A. ; Greer , H. A. ; Kelley , W. ; Jr.: Embree , M. C. ; Townsend , J. D. ; Beam , C. F. Preparation of 1H-pyrazole-5-carboxamides from dilithiated C(α),N-phenylhydrazones and lithiated ethyl oxanilates or lithiated ethyl oxamate . J. Heterocycl. Chem . 2001 , 38 , 691 – 694 .
  • Meierhoefer , M. A. ; Dunn , S. P. ; Hajiaghamohseni , L. M. ; Walters , M. J. ; Embree , M. C. ; Grant , S. P. ; Downs , J. R. ; Townsend , J. D. ; Metz , C. R. ; Beam , C. F. ; Pennington , W.T. ; VanDerveer , D. G. ; Camper , N. D. Preparation of 2-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamides from polylithiated C(α),N-phenylhydrazones and methyl 2-(aminosulfonyl)benzoate . J. Heterocycl. Chem . 2005 , 42 , 1095 – 1099 .
  • Church , A. C. ; Koller , M. U. ; O'Grady , S. A. ; Beam , C. F. The preparation of 1H-pyrazole-5-propanoic and 1H-pyrazole-5-butanoic acids from C(α),N-dilithiated N-carboalkoxyhydrazones and succinic or glutaric acid anhydrides . Synth. Commun. 1996 , 26 , 2603 – 2611.
  • Eliel , E. L. ; Burgstahler , A. W. Synthesis of methyl phthalaldehydate and phthalaldehydic acid by the Rosenmund reduction. J. Am. Chem. Soc . 1949, 71, 2251–2252.
  • Mirone , P. ; Vampiri , M. The infrared spectra at 2.7 and 5 µ of some substances containing the amino group. Atti. Accad. Nazl. Lincei., Rend. Classe Sci. Fis., Mat e Nat . 1952 , 583 ; Chem. Abstr . 1952 , 46 , 9423.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.