Synthesis and oxidative cleavage of 1-and 2-alkyl derivatives of (exo,exo)5,6-dihydroxy-4,5,6,7-tetrahydro-4,7,-methanoindazoles

被引：7

作者：

García, MD

Caamaño, O

Fernández, F

Figueira, MJ

Gómez, G

机构：

[1] Univ Santiago de Compostela, Fac Farm, Dept Quim Organ, Santiago De Compostela 15782, Spain

[2] Univ Vigo, Fac Ciencias Lagoas Marcosende, Dept Quim Organ, Vigo 36200, Spain

来源：

SYNTHESIS-STUTTGART | 2003年 / 14期

关键词：

indazoles; pyrazoles; heterocycles; alkylations; cleavage; nucleosides;

D O I：

10.1055/s-2003-41047

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of hydrazine with exo,exo-3-hydroxymethylene-5, 6-isopropylidenedioxybicyclo[2.2.1]heptan-2-one led to norbornenepyrazole 7, which was converted to its 1- and 2-alkyl derivatives. Deprotection of the vicinal hydroxyls, oxidative cleavage of the resulting glycol and reduction of the dialdehyde so obtained afforded 1- and 2-alkylcyclopenta[c]pyrazole-4,6-dimethanols, which are of interest as intermediates in the preparation of nucleoside analogues derived from 1H- and 2H-cyclopenta[c]pyrazole.

引用

页码：2138 / 2144

页数：7

共 50 条

[1] Two derivatives of lithium isodicyclopentadienide: [(1,2,3,3a,7a-eta)-4,5,6,7-tetrahydro-4,7-methanoindenido](N,N,N'N'-tetramethylethylenediamine)lithium and bis(1,4,7,10-tetraoxacyclododecane)lithium(1+) Bis[(1,2,3,3a,7a-eta)-4,5,6,7-tetrahydro-4,7-methanoindenido]lithate(1-)
Gallucci, JC
Sivik, MR
Paquette, LA
Zaegel, F
Meunier, P
Gautheron, B
[J]. ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1996, 52 : 1673 - 1679
[2] REGIOSELECTIVE SYNTHESIS OF THE HOMOCHIRAL LIGAND (4S,7R)-7,8,8-TRIMETHYL-4,5,6,7-TETRAHYDRO-4,7-METHANOINDAZOL-2-YL-INDAZOL-1'-YLMETHANE
LOPEZ, MC
JAGEROVIC, N
BALLESTEROS, P
[J]. TETRAHEDRON-ASYMMETRY, 1994, 5 (10) : 1887 - 1890
[3] Synthesis of 2-R-1-vinyl-4,5,6,7-tetrahydro-4,5,7-trimethylpyrrolo[3,2-c]pyridines
Borisova, TN
Bonifas, N
Voskresenskii, LG
Chernishev, AL
Varlamov, AV
Krapivko, AP
[J]. KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2004, (11): : 1709 - 1716
[4] Chiral annulated cyclopentadienyl Ligands:: Synthesis and crystal structure of both exo and endo Rh{η5-Cp′}(cod)} [Cp′ = (4S,7R)-1,2,3-triphenyl-4,8,8-trimethyl-1H,4,5,6,7-tetrahydro-4,7-methanoindenyl]
Ramsden, JA
Milner, DJ
Adams, H
Bailey, NA
Hempstead, PD
White, C
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 551 (1-2) : 355 - 366
[5] PSEUDO-SUGARS .22. SYNTHESIS OF PSEUDO-SUGAR DERIVATIVES FROM 5EXO, 6EXO-DIHYDROXY-ENDO AND EXO-7-OXABICYCLO[2.2.1]HEPTANE-2-CARBOXYLIC ACIDS
OGAWA, S
UEMURA, M
FUJITA, T
[J]. CARBOHYDRATE RESEARCH, 1988, 177 : 213 - 221
[6] SOLUBLE POLYIMIDES WITH POLYALICYCLIC STRUCTURE .1. POLYIMIDES FROM BICYCLO[2.2.2]OCT-7-ENE-2-EXO,3-EXO,5-EXO,6-EXO-TETRACARBOXYLIC 2,3/5,6-DIANHYDRIDES
ITAMURA, S
YAMADA, M
TAMURA, S
MATSUMOTO, T
KUROSAKI, T
[J]. MACROMOLECULES, 1993, 26 (14) : 3490 - 3493
[7] CHELATE SYNTHESIS OF DERIVATIVES OF 7-DIAMINOMETHYLENE-4,5,6,7-TETRAHYDRO-2H-INDAZOL-6-ONE
DOROKHOV, VA
GORDEEV, MF
PREZENT, MA
[J]. BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1991, 40 (02): : 457 - 457
[8] THE CRYSTAL-STRUCTURE OF TRANS-NONACHLOR, [1-EXO, 2-ENDO, 3-EXO-4,5,6,7,8,8-NONACHLORO-3A,4,7,7A-TETRAHYDRO-4,7-METHANOINDANE]
KENNARD, CHL
SMITH, G
SCHILLER, G
[J]. ZEITSCHRIFT FUR KRISTALLOGRAPHIE, 1985, 171 (3-4): : 303 - 311
[9] (+/-)-1-EXO-HYDROXY-4,5,6,7,8,8-HEXACHLORO-4,7-ENDO-3A,7A-ENDO-3A,4,7,7A-TETRAHYDRO-4,7-METHANOINDENE
KENNARD, CHL
HOVMOLLER, S
HODGSON, PG
SMITH, G
[J]. ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1978, 34 (OCT): : 3116 - 3118
[10] NOTES ON THE SYNTHESIS OF SULFONATED DERIVATIVES OF 5,6,7,8-TETRAHYDRO-1-NAPHTHYLAMINE AND 5,6,7,8-TETRAHYDRO-2-NAPHTHYLAMINE
COURTIN, A
[J]. HELVETICA CHIMICA ACTA, 1981, 64 (02) : 572 - 578

← 1 2 3 4 5 →