Synthesis of a Dihydroxy-Substituted Aminoxyl Spin Label and its Crown Ether and Cyclic Diester Derivatives

1993 ◽  
Vol 48 (4) ◽  
pp. 505-510 ◽  
Author(s):  
Yong-Kang Zhang ◽  
De-Kang Shen
Keyword(s):  
Crown Ether ◽  
Intramolecular Cyclization ◽  
Spin Label ◽  
Cyclic Ether ◽  
Synthetic Approach ◽  
Aminoxyl Radicals

A novel dihydroxy-substituted aminoxyl spin label, 4-hydroxy-3-(3'-hydroxypropyl)-2,2,6,6-tetramethylpiperidine-1-oxy (5), has been prepared. From this aminoxyl radical, a spin-labeled crown ether, 16,16,18,18-tetramethyl-2,5,8,11-tetraoxa-17-azabicyclo[ 13,4,0]-nonadecane-17-oxy (12), and a spin-labeled cyclic diester, 16,16,18,18-tetramethyl-3,10-dioxo-2,5,8,11-tetraoxa-17-azabicyclo[13,4,o]nonadecane-17-oxy (13), have been acquired. Other four new stable aminoxyl radicals 8,9,10, and 11 have also been obtained within the synthetic approach. It has been demonstrated that the cyclic ether compound (7) is generated by the reduction of its corresponding lactone which is sidely derived from the oxo-reduced species of 3 by intramolecular cyclization.

Diversity-Oriented Synthesis via Catalyst-Free Addition of Ketones to [e]-Fused 1H-Pyrrole-2,3-diones

Synthesis ◽  
2018 ◽  
Vol 50 (24) ◽  
pp. 4897-4904 ◽  
Author(s):  
Ekaterina Stepanova ◽  
Andrey Maslivets ◽  
Svetlana Kasatkina ◽  
Maksim Dmitriev
Keyword(s):  
Intramolecular Cyclization ◽  
Aromatic Hydrocarbons ◽  
Michael Addition ◽  
Aldol Reaction ◽  
Synthetic Approach ◽  
Reaction Conditions ◽  
Diversity Oriented Synthesis ◽  
Catalyst Free ◽  
Solvent Free Conditions ◽  
Reaction Proceeds

A facile synthetic approach towards two distinct pyrrole-based heterocyclic scaffolds has been developed by the interaction of 1H-pyrrole-2,3-diones fused at the [e]-side to a 1,4-benzoxazin-2-one or quinoxalin-2(1H)-one moiety with ketones. The described interaction proceeds either as an aldol reaction or as a Michael addition/intramolecular cyclization depending on the reaction conditions. The disclosed aldol reaction proceeds with good diastereoselectivity under catalyst-free conditions when the reaction is carried out in aromatic hydrocarbons. Products of the cascade Michael addition/intramolecular cyclization reaction are predominantly formed under catalyst-free and solvent-free conditions. The proposed strategy provides facile access to pharmaceutically interesting pyrrole-based polyheterocycles.

A Synthetic Approach to Macrocyclic, Chiral Phosphane Derivatives with Crown-Ether-Like Structures

2006 ◽  
Vol 2006 (1) ◽  
pp. 154-161 ◽  
Author(s):  
Agnès Theil ◽  
Julien Hitce ◽  
Pascal Retailleau ◽  
Angela Marinetti
Keyword(s):  
Crown Ether ◽  
Synthetic Approach

scholarly journals A Facile Synthesis of (±)-Heliannuol-D

2013 ◽  
Vol 8 (9) ◽  
pp. 1934578X1300800 ◽  
Author(s):  
Tao Zhang ◽  
Liang-Zhu Huang ◽  
You-Qiang Li ◽  
Yimg-Meng Xu ◽  
Zhen-Ting Du
Keyword(s):  
Intramolecular Cyclization ◽  
Cost Effective ◽  
Synthetic Approach ◽  
Lead Compound ◽  
Facile Synthesis ◽  
New Generation

A facile synthesis of (±)-heliannuol-D 1, which serves as an allelopathic chemical in nature and a potential lead compound in the search for new herbicides, has been achieved in a linear 11 steps, together with its epimer. The synthesis commenced with 4-methoxy-3-methyl-acetophenone, through the Baeyer-Villiger reaction, lithiation and addition, epoxidation and intramolecular cyclization to give (±)-heliannuol-D (1) and its epimer (1a) in 32.6% overall yield. Our synthetic approach is cost-effective; this will be helpful in applying this kind of compound for the development of a new generation of agrochemicals.

Base mediated 7-exo-dig intramolecular cyclization of Ugi–propargyl precursors: a highly efficient and regioselective synthetic approach toward diverse 1,4-benzoxazepine-5(2H)-ones

2014 ◽  
Vol 12 (29) ◽  
pp. 5346-5350 ◽  
Author(s):  
Shashi Pandey ◽  
S. Vinod Kumar ◽  
Ruchir Kant ◽  
Prem M. S. Chauhan
Keyword(s):  
Intramolecular Cyclization ◽  
Synthetic Approach ◽  
Metal Free ◽  
Highly Efficient

A metal-free facile and efficient two-step synthetic protocol for the preparation of 1,4-benzoxazepine-5(2H)-one derivatives has been developed.

A synthetic approach to crown ether analogs by the remote photocyclization with a pai system of phthalimide and methylthio groups

1982 ◽  
Vol 23 (30) ◽  
pp. 3077-3080 ◽  
Author(s):  
Masao Wada ◽  
Hideo Nakai ◽  
Yasuhiko Sato ◽  
Yuichi Kanaoka
Keyword(s):  
Crown Ether ◽  
Synthetic Approach
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