Cyclic Amino Alcohols Research Articles

Radical cyclizations of oxime ethers connected with aldehydes or ketones : A new entry to cyclic amino alcohols

Oxime ethers connected by a tether to aldehydes or ketones efficiently cyclize in a free radical cyclization which is mediated by tributyltin hydride and provide a new entry to the cyclic amino alcohols.

ChemInform Abstract: Highly Diastereomer Selective Acylation of 2,5‐Dialkylpyrrolidines. A Versatile Route to trans‐2,5‐Disubstituted Cyclic Amino Alcohols.

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Highly Diastereomer Selective Acylation of 2,5-Dialkylpyrrolidines. A Versatile Route to trans-2,5-Disubstituted Cyclic Amino Alcohols

Diastereoisomeric mixtures of cis- and trans- disubstituted pyrrolidines are separated by kinetically controlled acylation with benzyl chloroformate

Thioanalogues of anti-tumor antibiotics. II. Synthesis and preliminary in vitro cytotoxicity evaluation of tricyclic [1,4]benzothiazepine derivatives

The synthesis of tricyclic [1,4]benzothiazepine derivatives starting from optically active cyclic amino acids and amino alcohols is described. The absolute configurations of the target compounds were assigned by X-ray and 1H-NMR analyses and by molecular modeling studies. The cytotoxic activity of the tricyclic derivatives was tested in vitro by growth inhibition assays using murine L1210 and human lymphoblastic CCRF-CEM leukemias. Compounds 5, 9, and 10 exhibited marked cytotoxic activity.

ChemInform Abstract: Synthesis of Cyclic Amines and Their Alkyl Derivatives from Amino Alcohols Over Supported Copper Catalysts.

Abstract Cyclization of amino alcohols over copper supported on γ-alumina and magnesia was found to be an efficient method for the synthesis of cyclic amines, their alkyl derivatives and in some instances also their dehydro derivatives. Reactions were carried out in the temperature range 200–300°C using a continuous fixed-bed reactor and methanol or ethanol as solvent. The selectivities with respect to the different products depended markedly on the reaction temperature and the catalyst used. The amino alcohols used as reactants were 3-amino-1-propanol, 4-amino-1-butanol, 5-amino-1-pentanol and 6-amino-1-hexanol. The reaction of 3-amino-1-propanol was unspecific and led to various fragmentation products. In contrast, the reaction of 4-amino- 1-butanol yielded either pyrrolidine (selectivity 62%), N-methylpyrrolidine (71%) or Δ 1 -dehydropyrrolidine (47%), depending on the conditions. The reaction of 5-amino-1-pentanol led either to piperidine (99%) or N -methylpiperidine (93%). Hexahydro-1 H -azepine (95%) was the main product of the cyclization of 6-amino-1-hexanol.

Transformation of organic compounds in the presence of metal complexes V. Cyclization of aminoalcohols on a ruthenium complex

In the presence of RuCl 2(PPh 3) 3 as catalyst at 150–180°C, N-substituted aminoalcohols are cyclized to N-substituted azacycloalkanes in good yields.

Synthesis of cyclic amines and their alkyl derivatives from amino alcohols over supported copper catalysts

Cyclization of amino alcohols over copper supported on γ-alumina and magnesia was found to be an efficient method for the synthesis of cyclic amines, their alkyl derivatives and in some instances also their dehydro derivatives. Reactions were carried out in the temperature range 200–300°C using a continuous fixed-bed reactor and methanol or ethanol as solvent. The selectivities with respect to the different products depended markedly on the reaction temperature and the catalyst used. The amino alcohols used as reactants were 3-amino-1-propanol, 4-amino-1-butanol, 5-amino-1-pentanol and 6-amino-1-hexanol. The reaction of 3-amino-1-propanol was unspecific and led to various fragmentation products. In contrast, the reaction of 4-amino- 1-butanol yielded either pyrrolidine (selectivity 62%), N-methylpyrrolidine (71%) or Δ 1-dehydropyrrolidine (47%), depending on the conditions. The reaction of 5-amino-1-pentanol led either to piperidine (99%) or N-methylpiperidine (93%). Hexahydro-1 H-azepine (95%) was the main product of the cyclization of 6-amino-1-hexanol.

ChemInform Abstract: Saturated Heterocycles. Part 135. Cyclic Aminoalcohols and Related Compounds. Part 29. Synthesis of Condensed‐Sheleton cis‐ and trans‐2‐Phenylimino‐ and 2‐Methyliminotetrahydro‐1,3‐thiazines and ‐1,3‐oxazines.

AbstractReaction of the cyclopentane derivatives (I) with the isothiocyanate (II) followed by treatment of the products (III) with HCl or with MeI (V) and alkali gives rise to the heterocycles (IV) or (VI), respectively.

ChemInform Abstract: Stereochemical Studies. Part 109. Cyclic Aminoalcohols and Related Compounds. Part 30. A Simple Route to N‐Substituted cis‐ and trans‐2‐Hydroxymethylcycloalkylamines and Related Alicyclic 1,3‐Aminoalcohols.

ChemInformVolume 19, Issue 13 Isocyclic Compounds ChemInform Abstract: Stereochemical Studies. Part 109. Cyclic Aminoalcohols and Related Compounds. Part 30. A Simple Route to N-Substituted cis- and trans-2-Hydroxymethylcycloalkylamines and Related Alicyclic 1,3-Aminoalcohols. F. + FUELOEP, Inst. Pharm. Chem., Univ. Med. Sch., H-6720 SzegedSearch for more papers by this authorI. HUBER, Inst. Pharm. Chem., Univ. Med. Sch., H-6720 SzegedSearch for more papers by this authorG. BERNATH, Inst. Pharm. Chem., Univ. Med. Sch., H-6720 SzegedSearch for more papers by this author F. + FUELOEP, Inst. Pharm. Chem., Univ. Med. Sch., H-6720 SzegedSearch for more papers by this authorI. HUBER, Inst. Pharm. Chem., Univ. Med. Sch., H-6720 SzegedSearch for more papers by this authorG. BERNATH, Inst. Pharm. Chem., Univ. Med. Sch., H-6720 SzegedSearch for more papers by this author First published: March 29, 1988 https://doi.org/10.1002/chin.198813148Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume19, Issue13March 29, 1988 RelatedInformation

ChemInform Abstract: Stereochemical Studies. Part 80. Cyclic Aminoalcohols and Related Compounds. Part 26. Preparation of cis‐2‐(Alkylaminomethyl)‐ und (Aralkylaminomethyl)‐1‐cyclanols (V) from Olef ins (I) via the 5,6‐Dihydro‐4H‐1,3‐oxazine Derivatives (III).

ChemInform Abstract: Stereochemical Studies. Part 80. Cyclic Aminoalcohols and Related Compounds. Part 26. Preparation of cis‐2‐(Alkylaminomethyl)‐ und (Aralkylaminomethyl)‐1‐cyclanols (V) from Olef ins (I) via the 5,6‐Dihydro‐4H‐1,3‐oxazine Derivatives (III).

ChemInform Abstract: STEREOCHEMICAL STUDIES PART 23, CYCLIC AMINOALCOHOLS AND RELATED COMPOUNDS PART 13, N‐O ACYL MIGRATION IN STEREOISOMERIC 2‐BENZAMIDOMETHYL‐4‐T‐BUTYLCYCLOHEXANOLS, THE PREFERRED TRANSITION STATE IN THE ACYL MIGRATION OF RELATED CYCLIC 1,3‐AMINOALCOHOLS

Chemischer InformationsdienstVolume 6, Issue 47 Preparative Organic Chemistry ChemInform Abstract: STEREOCHEMICAL STUDIES PART 23, CYCLIC AMINOALCOHOLS AND RELATED COMPOUNDS PART 13, N-O ACYL MIGRATION IN STEREOISOMERIC 2-BENZAMIDOMETHYL-4-T-BUTYLCYCLOHEXANOLS, THE PREFERRED TRANSITION STATE IN THE ACYL MIGRATION OF RELATED CYCLIC 1,3-AMINOALCOHOLS G. BERNATH, G. BERNATHSearch for more papers by this authorK. L. LANG, K. L. LANGSearch for more papers by this authorM. TICHY, M. TICHYSearch for more papers by this authorM. PANKOVA, M. PANKOVASearch for more papers by this author G. BERNATH, G. BERNATHSearch for more papers by this authorK. L. LANG, K. L. LANGSearch for more papers by this authorM. TICHY, M. TICHYSearch for more papers by this authorM. PANKOVA, M. PANKOVASearch for more papers by this author First published: November 25, 1975 https://doi.org/10.1002/chin.197547111AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume6, Issue47November 25, 1975 RelatedInformation

Stereochemical studies‐XIV: Cyclic amino alcohols and related compounds‐VII

Abstract1,3‐Tetrahydro‐oxazine‐2‐ones were prepared by the reaction of cis‐ and trans‐2‐hydroxymethylcyclohexylamine, as well as cis‐ and trans‐2‐aminomethylcyclohexanol with carbamide. Their structure and stereochemical purity were proved by IR and NMR investigations. With the help of the NMR spectra the conformation of these compounds was established. The trans isomers exist in stable chair‐chair conformation. Two chair‐chair conformations are possible in the case of the cis isomers; one in which the heteroatom and the methylene group of the heteroring are axial and equatorial, respectively and the second in which their positions are reversed. It was proved that the cis isomers are conformationally homogeneous, having the hetero atom in axial position.

Stereochemical studies—XVII: Cyclic aminoalcohols and related compounds—IX synthesis and NMR study of stereoisomeric cis- and trans-tetramethylene- and pentamethylene-1,3-oxazine-2-ones

Isomeric tetramethylene- and pentamethylene-1,3-oxazine-2-ones (9–12 and13–16) have been synthesized, derived from cis- and trans-2-aminomethylcyclohexanol (1,2), cis- and trans-2-hydroxymethylcyclohexylamine (3,4) and from the corresponding cycloheptane analogues (5–8), respectively. The stereospecific synthesis of the aminoalcohols5–8 is described. A comparative NMR analysis of13–16 and the tetramethylene analogues (9–12) is given.

Carbanilic acid esters of cyclic amino alcohols. 5. Local anesthetic potency of the enantiomers of two N-butyl-3-piperidyl carbanilates

Carbanilic acid esters of cyclic amino alcohols. 5. Local anesthetic potency of the enantiomers of two N-butyl-3-piperidyl carbanilates

Studies on carbanilic acid esters of cyclic amino alcohols. 4. Esters of pyrrolidinols and piperidinols as local anesthetics.

Studies on carbanilic acid esters of cyclic amino alcohols. 4. Esters of pyrrolidinols and piperidinols as local anesthetics.

Blockade of the action current in single nodes of ranvier from frog nerve by physostigmine and certain amino derivatives

The effects produced by physostigmine and a limited series of aromatic esters derived from cis- and trans-2-dimethylaminocyclohexanol on electrical parameters associated with the action current from the single node preparation of frog sciatic nerve have been briefly studied. In general, the attenuation results of drug action on the single node parallel closely those previously obtained with the polyfiber nerve preparation. Physostigmine attenuates the amplitude of the action current in rough proportion to the concentration of tertiary drug species present in solution, but the diminution in peak height is accompanied by a spreading of the wave on the time axis, leading to an enhanced current-time integral. In contrast, the benzilate and diphenyl acetate esters of the parent cyclic amino alcohols are more powerful than physostigmine in attenuating the nodal action current, approaching the strength of the potent agent veratridine, but they do not simultaneously distort the shape of the residual current curve. Each of the effective current-attenuating agents in the series also produces significant increases in the threshold voltage requirements of the nodal preparation. Both the current attenuations and the threshold changes (except for physostigmine) are fairly readily reversed on removal of the blocking agents. Attempts at correlation of nodal current attenuating strengths with in vitro anticholinesterasic potencies fail markedly in this series of amino alcohol derivatives.

Stereochemistry of Cyclic Amino-alcohols. Inversion, Retention and Participation

Stereochemistry of Cyclic Amino-alcohols. Inversion, Retention and Participation