Synthesis of Enantiopure Primary Amines by Stereoselective Ring Opening of Chiral Octahydro-1,3-benzoxazines by Grignard and Organoaluminum Reagents†

1996 ◽  
Vol 61 (12) ◽  
pp. 4130-4135 ◽  
Author(s):  
Celia Andrés ◽  
Javier Nieto ◽  
Rafael Pedrosa ◽  
Nieves Villamañán
Keyword(s):  
Ring Opening ◽  
Primary Amines

CARCINOGENICITY OF LACTONES: I. THE REACTION OF 4-METHYLBUTENO- AND 4-METHYLBUTANO-γ-LACTONES WITH PRIMARY AMINES

1966 ◽  
Vol 44 (9) ◽  
pp. 1059-1068 ◽  
Author(s):  
J. Bryan Jones ◽  
John M. Young
Keyword(s):  
Magnetic Resonance ◽  
Michael Addition ◽  
Ring Opening ◽  
Proton Magnetic Resonance ◽  
Mechanisms Of Action ◽  
Reaction Pathways ◽  
Nucleophilic Attack ◽  
Primary Amines ◽  
Acid Lactone ◽  
The Michael Addition

As the first stage in the investigations of the mechanisms of action of carcinogenic lactones, the reactions of 4-hydroxypent-2-enoic acid lactone (II, R = CH3), which is a carcinogen, and of the non-carcinogenic 4-hydroxypent-3-enoic (III, R = CH3) and 4-hydroxypentanoic (IV, R = CH3) acid lactones with methylamine and benzylamine have been studied. As expected, the carcinogenic lactone reacts to give the Michael addition products, whereas both inactive lactones undergo ring opening by nucleophilic attack at the carbonyl group. From the relative rates of reaction of the amines with the lactones it is concluded that the induction of tumors by II (R = CH3) does not involve alkylation of biological primary alkylamino groups. The proton magnetic resonance spectra of the products enable the different reaction pathways to be distinguished readily, and may provide the basis for rapid physicochemical screening of alkylation agents that are potential carcinogens.

Asymmetric Synthesis of 2,3-Dihydropyrroles by Ring-Opening/Cyclization of Cyclopropyl Ketones Using Primary Amines

2014 ◽  
Vol 54 (1) ◽  
pp. 227-230 ◽  
Author(s):  
Yong Xia ◽  
Xiaohua Liu ◽  
Haifeng Zheng ◽  
Lili Lin ◽  
Xiaoming Feng
Keyword(s):  
Asymmetric Synthesis ◽  
Ring Opening ◽  
Primary Amines ◽  
Cyclopropyl Ketones

scholarly journals An efficient and atom-economical route to N-aryl amino alcohols from primary amines

RSC Advances ◽  
2018 ◽  
Vol 8 (60) ◽  
pp. 34304-34308 ◽  
Author(s):  
Zhen Xiao ◽  
Juanjuan Li ◽  
Qiang Yue ◽  
Qian Zhang ◽  
Dong Li
Keyword(s):  
Ring Opening ◽  
Amino Alcohols ◽  
Primary Amines ◽  
Ring Opening Reaction ◽  
Novel Method

A novel method for generation of N-aryl amino alcohols from N,N-disubstituted picolinamides through reduction/ring-opening reaction with NaBH4 was developed.

scholarly journals Synthesis of a series of vicinal diamines with potential biological activity

2004 ◽  
Vol 2 (4) ◽  
pp. 686-695 ◽  
Author(s):  
Vanya Kurteva ◽  
Maria Lyapova
Keyword(s):  
Biological Activity ◽  
Anticancer Activity ◽  
Ring Opening ◽  
Styrene Oxide ◽  
Primary Amines ◽  
Reaction Series ◽  
Cisplatin Analogues ◽  
Biological Interest ◽  
Aziridinium Ions ◽  
Vicinal Diamines

AbstractA broad range of vicinal diamines based on styrene oxide are synthesisedvia mixtures of regioisomeric amino alcohols. The ring opening of the intermediate aziridinium ions by primary amines proceeds with high regioselectivity, leading to the target diamines as single regioisomers for all reaction series. The compounds are of potential biological interest as ligands for cisplatin analogues. Anticancer activity tests of both groups of compounds are in progress.

ChemInform Abstract: Asymmetric Synthesis of 2,3-Dihydropyrroles by Ring-Opening/Cyclization of Cyclopropyl Ketones Using Primary Amines.

ChemInform ◽  
2015 ◽  
Vol 46 (21) ◽  
pp. no-no
Author(s):  
Yong Xia ◽  
Xiaohua Liu ◽  
Haifeng Zheng ◽  
Lili Lin ◽  
Xiaoming Feng
Keyword(s):  
Asymmetric Synthesis ◽  
Ring Opening ◽  
Primary Amines ◽  
Cyclopropyl Ketones

scholarly journals Ring Opening of Donor–Acceptor Cyclopropanes with N-Nucleo­philes

Synthesis ◽  
2017 ◽  
Vol 49 (14) ◽  
pp. 3035-3068 ◽  
Author(s):  
Ekaterina Budynina ◽  
Konstantin Ivanov ◽  
Ivan Sorokin ◽  
Mikhail Melnikov
Keyword(s):  
Ring Opening ◽  
Building Blocks ◽  
Simple Approach ◽  
Secondary Amines ◽  
Primary Amines ◽  
Pyrrole Derivatives ◽  
Heteroaromatic Compounds ◽  
Azide Ion ◽  
Ring Opening Reactions ◽  
Donor Acceptor

Ring opening of donor–acceptor cyclopropanes with various N-nucleophiles provides a simple approach to 1,3-functionalized compounds that are useful building blocks in organic synthesis, especially in assembling various N-heterocycles, including natural products. In this review, ring-opening reactions of donor–acceptor cyclopropanes with amines, amides, hydrazines, N-heterocycles, nitriles, and the azide ion are summarized.1 Introduction2 Ring Opening with Amines3 Ring Opening with Amines Accompanied by Secondary Processes Involving the N-Center3.1 Reactions of Cyclopropane-1,1-diesters with Primary and Secondary Amines3.1.1 Synthesis of γ-Lactams3.1.2 Synthesis of Pyrroloisoxazolidines and -pyrazolidines3.1.3 Synthesis of Piperidines3.1.4 Synthesis of Azetidine and Quinoline Derivatives3.2 Reactions of Ketocyclopropanes with Primary Amines: Synthesis of Pyrrole Derivatives3.3 Reactions of Сyclopropane-1,1-dicarbonitriles with Primary Amines: Synthesis of Pyrrole Derivatives4 Ring Opening with Tertiary Aliphatic Amines5 Ring Opening with Amides6 Ring Opening with Hydrazines7 Ring Opening with N-Heteroaromatic Compounds7.1 Ring Opening with Pyridines7.2 Ring Opening with Indoles7.3 Ring Opening with Di- and Triazoles7.4 Ring Opening with Pyrimidines8 Ring Opening with Nitriles (Ritter Reaction)9 Ring Opening with the Azide Ion10 Summary

Merging Transition-Metal Catalysis with Phthalimides: A New Entry to Useful Building Blocks

Synthesis ◽  
2018 ◽  
Vol 50 (21) ◽  
pp. 4216-4228 ◽  
Author(s):  
Rafael Gramage-Doria ◽  
Yu-Chao Yuan ◽  
Christian Bruneau
Keyword(s):  
Transition Metal ◽  
Ring Opening ◽  
Building Blocks ◽  
Short Review ◽  
Transition Metal Catalysts ◽  
Primary Amines ◽  
Metal Catalysis ◽  
Biologically Relevant ◽  
Multistep Synthesis ◽  
Carbonyl Reduction

Phthalimides have found their main application in organic synthesis as protecting groups for primary amines during the multistep synthesis of biologically relevant targets. On the other hand, phthalimide functionalization is rather challenging and it is traditionally associated with the use of over-stoichiometric amounts of environmentally hazardous reagents. In this short review, we describe and discuss how, in the last decades, transition-metal catalysts have provided useful organic building blocks after selective transformation of the phthalimide skeleton in a more efficient and sustainable manner.1 Introduction2 Partial Carbonyl Reduction3 Full Carbonyl Reduction4 Aromatic Ring Reduction5 Five-Membered-Ring Opening6 Conclusion

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