Montmorillonite KSF clay-promoted synthesis of enantiomerically pure 5-substituted pyrazoles from 2,3-dihydro-4H-pyran-4-ones

被引：17

作者：

Yadav, JS ^{[1
]}

Reddy, BVS ^{[1
]}

Srinivas, M ^{[1
]}

Prabhakar, A ^{[1
]}

Jagadeesh, B ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 31期

关键词：

glycals; dihydropyranones; hydrazines; pyrazoles;

D O I：

10.1016/j.tetlet.2004.06.031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2,3-Dihydro-4H-pyran-4-ones derived from D-glucal undergo rapid condensation with aryl hydrazines in the presence of montmorillonite KSF clay under mild conditions to afford a novel class of chiral 5-substituted pyrazoles in good yields with high selectivity. The stereochemical assignments of the products were achieved by NMR Studies. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：6033 / 6036

页数：4

共 50 条

[31] NEW SYNTHESIS OF SUBSTITUTED 3,5-DIHYDRO-4H-2,3-BENZODIAZEPIN-4-ONES
SOTIRIADIS, A
CATSOULA.P
THEODORO.D
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1974, 11 (03) : 401 - 403
[32] Highly efficient indium(III)-mediated cyclisation of 5-hydroxy-1,3-diketones to 2,3-dihydro-4H-pyran-4-ones; mechanistic insights from in situ Fourier transform infrared spectroscopy
Andrews, Philip C.
Gee, William J.
Junk, Peter C.
Krautscheid, Harald
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (03) : 698 - 705
[33] An effective protocol for the synthesis enantiomerically pure 4-substituted oxetane-2-ones
Balakier, Tomasz
Chaladaj, Wojciech
Jurczak, Janusz
Adamus, Grazyna
Kowalczuk, Marek
TETRAHEDRON, 2013, 69 (24) : 4990 - 4993
[34] SYNTHESIS OF SOME 3 (OR 5)-SUBSTITUTED 5(OR3)-(2-HYDROXYALKYL)-PYRAZOLES FROM 2,3-DIHYDRO-4-PYRONES
GELIN, S
DESHAYES, C
SYNTHESIS-STUTTGART, 1978, (12): : 900 - 901
[35] Indium-mediated regioselective mono-allylation of 1,5-dicarbonyl compounds and dehydrative cyclization to 2,3-dihydro-4H-pyran-4-ones and 3,4-dihydro-2H-[1,4]oxazines
Kim, Sung Hwan
Lee, Sangku
Kim, Se Hee
Lim, Jin Woo
Kim, Jae Nyoung
TETRAHEDRON LETTERS, 2012, 53 (37) : 4979 - 4983
[36] CONVENIENT PREPARATIONS OF 2,3-DIHYDRO-4H-PYRAN-4-ONES FROM D-GLUCAL TRIACETATE - SELECTIVE OXIDATIONS OF ALYLLIC ACETATES AND ALLYLIC SILYL ETHERS USING N-BROMOSUCCINIMIDE
BOUILLOT, A
KHAC, DD
FETIZON, M
GUIR, F
MEMORIA, Y
SYNTHETIC COMMUNICATIONS, 1993, 23 (15) : 2071 - 2081
[37] A SIMPLE, ONE-POT SYNTHESIS OF 2,3-DIHYDRO-4H-PYRAN-4-ONES VIA THE ACID-CATALYZED [4+2]-CYCLOADDITION OF 1-ALKOXY-3-TRIMETHYLSILYLOXY-1,3-BUTADIENES WITH ALDEHYDES
ABEN, RW
SCHEEREN, HW
SYNTHESIS-STUTTGART, 1982, (09): : 779 - 781
[38] A General Method for the Synthesis of 3-Substituted Tetrahydro- and 2,3-Dihydro-4H-thiopyran-4-ones
Synlett, 3 (261):
[39] A general method for the synthesis of 3-substituted tetrahydro- and 2,3-dihydro-4H-thiopyran-4-ones
Ward, DE
Gai, YZ
Lai, YJ
SYNLETT, 1996, (03) : 261 - &
[40] A NEW AMINE CATALYZED SYNTHESIS OF 2-SUBSTITUTED 2,3-DIHYDRO-4H-1,3-BENZOXAZIN-4-ONES
GAMMILL, RB
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (16): : 3340 - 3342

← 1 2 3 4 5 →