The Structures of Indazolin-3-one (=1,2-Dihydro-3H-indazol-3-one) and 7-Nitroindazolin-3-one

被引：8

作者：

Claramunt, Rosa M. ^{[1
]}

Sanza, Dionisia ^{[1
]}

Lopez, Concepcion ^{[1
]}

Pinilla, Elena ^{[2
]}

Rosario Torres, M. ^{[2
]}

Elguero, Jose ^{[3
]}

Nioche, Pierre ^{[4
]}

Raman, C. S. ^{[4
]}

机构：

[1] Univ Nacl Educ Distancia, Dept Quim Organ & Bioorgan, Fac Ciencias, E-28040 Madrid, Spain

[2] Univ Complutense Madrid, Dept Quim Inorgan 1, Lab Difracc Rayos X, Fac Ciencias Quim, E-28040 Madrid, Spain

[3] CSIC, Inst Quim Med, E-28006 Madrid, Spain

[4] Univ Texas Med Sch, Dept Biochem & Mol Biol, Houston, TX 77030 USA

来源：

HELVETICA CHIMICA ACTA | 2009年 / 92卷 / 10期

关键词：

MOLECULAR-ORBITAL METHODS; NMR CHEMICAL-SHIFTS; ANNULAR TAUTOMERISM; SOLID-STATE; X-RAY; DERIVATIVES; 3-INDAZOLINONE; HETEROCYCLES; BEHAVIOR; DATABASE;

D O I：

10.1002/hlca.200900119

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The existence of polymorphism in parent indazolin-3-one (=1,2-dihydro-3H-indazol-3-one; 1) is reported as well as an X-ray and NMR CPMAS study establishing that its 7-nitro derivative 2 exists as the 3-hydroxy tautomer. Absolute shieldings calculated at the GIAO/B3LYP/6-311 ++ G(d,p) level were used to determine the tautomeric oxo/hydroxy equilibrium in solution, i.e., always the 1H-indazol-3-ol tautomer predominates.

引用

页码：1952 / 1962

页数：11

共 46 条

[1] Theoretical estimation of the annular tautomerism of indazoles [J].

Alkorta, I ;

Elguero, J .

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2005, 18 (08) :719-724

[2] A density functional theoretical study of the influence of cavities and water molecules on tautomerism: the case of pyridones and 1,2,4-triazoles linked to crown ethers and esters [J].

Alkorta, I ;

Elguero, J .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2001, 38 (06) :1387-1391

[3] Applications of the Cambridge Structural Database in organic chemistry and crystal chemistry [J].

Allen, FH ;

Motherwell, WDS .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE CRYSTAL ENGINEERING AND MATERIALS, 2002, 58 :407-422

[4] The Cambridge Structural Database: a quarter of a million crystal structures and rising [J].

Allen, FH .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 2002, 58 (3 PART 1) :380-388

[5]

[Anonymous], 1997, PROGRAM REFINEMENT C

[6] THE STRUCTURE OF INDAZOLINONE AND DERIVATIVES IN THE SOLID-STATE AND IN SOLUTION - AN X-RAY AND NUCLEAR-MAGNETIC-RESONANCE STUDY [J].

BALLESTEROS, P ;

ELGUERO, J ;

CLARAMUNT, RM ;

FAURE, R ;

FOCESFOCES, MD ;

CANO, FH ;

ROUSSEAU, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1986, (11) :1677-1681

[7]

BERESIS RT, 2007, Patent No. 2008051403

[8]

Berger S., 2004, 200 MORE NMR EXPT, V3rd

[9] Statistical analysis of 13C and 15N NMR chemical shifts from GIAO/B3LYP/6-311++G** calculated absolute shieldings [J].

Blanco, Fernando ;

Alkorta, Ibon ;

Elguero, Jose .

MAGNETIC RESONANCE IN CHEMISTRY, 2007, 45 (09) :797-800

[10]

BLANDWARD PA, 1997, EUR J PHARMACOL, V326, P53

← 1 2 3 4 5 →