Stereochemistry of nitrogen heterocycles. 49. Synthesis and transformations of stereoisomeric 4-keto-2-methyl-n-chloro-trans-decahydroquinolines
Abstract Epimeric (with respect to the methyl group) stereoisomers of 4-keto-2-methyl-1-chloro-trans-decahydroquinoline were obtained, and their transformations under the influence of triethylamine were investigated. It was shown that the direction of the transformations depends on the steric orient...
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E-Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
1984 |
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| Umfang: |
7 |
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| Reproduktion: |
Springer Online Journal Archives 1860-2002 |
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| Übergeordnetes Werk: |
in: Chemistry of heterocyclic compounds - 1965, 20(1984) vom: Juni, Seite 643-649 |
| Übergeordnetes Werk: |
volume:20 ; year:1984 ; month:06 ; pages:643-649 ; extent:7 |
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| 245 | 1 | 0 | |a Stereochemistry of nitrogen heterocycles. 49. Synthesis and transformations of stereoisomeric 4-keto-2-methyl-n-chloro-trans-decahydroquinolines |
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| 520 | |a Abstract Epimeric (with respect to the methyl group) stereoisomers of 4-keto-2-methyl-1-chloro-trans-decahydroquinoline were obtained, and their transformations under the influence of triethylamine were investigated. It was shown that the direction of the transformations depends on the steric orientation of the methyl group and the molar ratio of the N-chloroamine and triethylamine. The N-chloroamine isomer with an equatorial methyl group undergoes dehydrochlorination in the presence of excess triethylamine to give 2-methyl-4-hydroxy-trans-5,6,7,8,9,10-hexahydroquinoline. With an equimolar amount of triethylamine in solution in CCl4 the principal reaction pathway becomes dehydrochlorination and subsequent chlorination to give 2-methyl-4-hydroxy-3-chloro-trans-5,6,7,8,9,10-hexahydroquinoline. The N-chloroamine isomer with an axial methyl group in the presence of both excess and, in particular, equimolar amounts of triethylamine undergoes, in addition to dehydrochlorination and chlorination in the β position of the piperidine ring, cis-trans isomerization and subsequent dehydrogenation with the primary formation of 2-methyl-4-hydroxy-3-chloro-5,6,7,8-tetrahydroquinoline. The mechanism of the transformations is examined. | ||
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(DE-627)NLEJ190390573 DE-627 ger DE-627 rakwb eng Stereochemistry of nitrogen heterocycles. 49. Synthesis and transformations of stereoisomeric 4-keto-2-methyl-n-chloro-trans-decahydroquinolines 1984 7 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Abstract Epimeric (with respect to the methyl group) stereoisomers of 4-keto-2-methyl-1-chloro-trans-decahydroquinoline were obtained, and their transformations under the influence of triethylamine were investigated. It was shown that the direction of the transformations depends on the steric orientation of the methyl group and the molar ratio of the N-chloroamine and triethylamine. The N-chloroamine isomer with an equatorial methyl group undergoes dehydrochlorination in the presence of excess triethylamine to give 2-methyl-4-hydroxy-trans-5,6,7,8,9,10-hexahydroquinoline. With an equimolar amount of triethylamine in solution in CCl4 the principal reaction pathway becomes dehydrochlorination and subsequent chlorination to give 2-methyl-4-hydroxy-3-chloro-trans-5,6,7,8,9,10-hexahydroquinoline. The N-chloroamine isomer with an axial methyl group in the presence of both excess and, in particular, equimolar amounts of triethylamine undergoes, in addition to dehydrochlorination and chlorination in the β position of the piperidine ring, cis-trans isomerization and subsequent dehydrogenation with the primary formation of 2-methyl-4-hydroxy-3-chloro-5,6,7,8-tetrahydroquinoline. The mechanism of the transformations is examined. Springer Online Journal Archives 1860-2002 Litvinenko, G. S. oth Voronenko, L. A. oth in Chemistry of heterocyclic compounds 1965 20(1984) vom: Juni, Seite 643-649 (DE-627)NLEJ188993940 (DE-600)2037128-7 1573-8353 nnns volume:20 year:1984 month:06 pages:643-649 extent:7 http://dx.doi.org/10.1007/BF00508674 GBV_USEFLAG_U ZDB-1-SOJ GBV_NL_ARTICLE AR 20 1984 6 643-649 7 |
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(DE-627)NLEJ190390573 DE-627 ger DE-627 rakwb eng Stereochemistry of nitrogen heterocycles. 49. Synthesis and transformations of stereoisomeric 4-keto-2-methyl-n-chloro-trans-decahydroquinolines 1984 7 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Abstract Epimeric (with respect to the methyl group) stereoisomers of 4-keto-2-methyl-1-chloro-trans-decahydroquinoline were obtained, and their transformations under the influence of triethylamine were investigated. It was shown that the direction of the transformations depends on the steric orientation of the methyl group and the molar ratio of the N-chloroamine and triethylamine. The N-chloroamine isomer with an equatorial methyl group undergoes dehydrochlorination in the presence of excess triethylamine to give 2-methyl-4-hydroxy-trans-5,6,7,8,9,10-hexahydroquinoline. With an equimolar amount of triethylamine in solution in CCl4 the principal reaction pathway becomes dehydrochlorination and subsequent chlorination to give 2-methyl-4-hydroxy-3-chloro-trans-5,6,7,8,9,10-hexahydroquinoline. The N-chloroamine isomer with an axial methyl group in the presence of both excess and, in particular, equimolar amounts of triethylamine undergoes, in addition to dehydrochlorination and chlorination in the β position of the piperidine ring, cis-trans isomerization and subsequent dehydrogenation with the primary formation of 2-methyl-4-hydroxy-3-chloro-5,6,7,8-tetrahydroquinoline. The mechanism of the transformations is examined. Springer Online Journal Archives 1860-2002 Litvinenko, G. S. oth Voronenko, L. A. oth in Chemistry of heterocyclic compounds 1965 20(1984) vom: Juni, Seite 643-649 (DE-627)NLEJ188993940 (DE-600)2037128-7 1573-8353 nnns volume:20 year:1984 month:06 pages:643-649 extent:7 http://dx.doi.org/10.1007/BF00508674 GBV_USEFLAG_U ZDB-1-SOJ GBV_NL_ARTICLE AR 20 1984 6 643-649 7 |
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(DE-627)NLEJ190390573 DE-627 ger DE-627 rakwb eng Stereochemistry of nitrogen heterocycles. 49. Synthesis and transformations of stereoisomeric 4-keto-2-methyl-n-chloro-trans-decahydroquinolines 1984 7 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Abstract Epimeric (with respect to the methyl group) stereoisomers of 4-keto-2-methyl-1-chloro-trans-decahydroquinoline were obtained, and their transformations under the influence of triethylamine were investigated. It was shown that the direction of the transformations depends on the steric orientation of the methyl group and the molar ratio of the N-chloroamine and triethylamine. The N-chloroamine isomer with an equatorial methyl group undergoes dehydrochlorination in the presence of excess triethylamine to give 2-methyl-4-hydroxy-trans-5,6,7,8,9,10-hexahydroquinoline. With an equimolar amount of triethylamine in solution in CCl4 the principal reaction pathway becomes dehydrochlorination and subsequent chlorination to give 2-methyl-4-hydroxy-3-chloro-trans-5,6,7,8,9,10-hexahydroquinoline. The N-chloroamine isomer with an axial methyl group in the presence of both excess and, in particular, equimolar amounts of triethylamine undergoes, in addition to dehydrochlorination and chlorination in the β position of the piperidine ring, cis-trans isomerization and subsequent dehydrogenation with the primary formation of 2-methyl-4-hydroxy-3-chloro-5,6,7,8-tetrahydroquinoline. The mechanism of the transformations is examined. Springer Online Journal Archives 1860-2002 Litvinenko, G. S. oth Voronenko, L. A. oth in Chemistry of heterocyclic compounds 1965 20(1984) vom: Juni, Seite 643-649 (DE-627)NLEJ188993940 (DE-600)2037128-7 1573-8353 nnns volume:20 year:1984 month:06 pages:643-649 extent:7 http://dx.doi.org/10.1007/BF00508674 GBV_USEFLAG_U ZDB-1-SOJ GBV_NL_ARTICLE AR 20 1984 6 643-649 7 |
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(DE-627)NLEJ190390573 DE-627 ger DE-627 rakwb eng Stereochemistry of nitrogen heterocycles. 49. Synthesis and transformations of stereoisomeric 4-keto-2-methyl-n-chloro-trans-decahydroquinolines 1984 7 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Abstract Epimeric (with respect to the methyl group) stereoisomers of 4-keto-2-methyl-1-chloro-trans-decahydroquinoline were obtained, and their transformations under the influence of triethylamine were investigated. It was shown that the direction of the transformations depends on the steric orientation of the methyl group and the molar ratio of the N-chloroamine and triethylamine. The N-chloroamine isomer with an equatorial methyl group undergoes dehydrochlorination in the presence of excess triethylamine to give 2-methyl-4-hydroxy-trans-5,6,7,8,9,10-hexahydroquinoline. With an equimolar amount of triethylamine in solution in CCl4 the principal reaction pathway becomes dehydrochlorination and subsequent chlorination to give 2-methyl-4-hydroxy-3-chloro-trans-5,6,7,8,9,10-hexahydroquinoline. The N-chloroamine isomer with an axial methyl group in the presence of both excess and, in particular, equimolar amounts of triethylamine undergoes, in addition to dehydrochlorination and chlorination in the β position of the piperidine ring, cis-trans isomerization and subsequent dehydrogenation with the primary formation of 2-methyl-4-hydroxy-3-chloro-5,6,7,8-tetrahydroquinoline. The mechanism of the transformations is examined. Springer Online Journal Archives 1860-2002 Litvinenko, G. S. oth Voronenko, L. A. oth in Chemistry of heterocyclic compounds 1965 20(1984) vom: Juni, Seite 643-649 (DE-627)NLEJ188993940 (DE-600)2037128-7 1573-8353 nnns volume:20 year:1984 month:06 pages:643-649 extent:7 http://dx.doi.org/10.1007/BF00508674 GBV_USEFLAG_U ZDB-1-SOJ GBV_NL_ARTICLE AR 20 1984 6 643-649 7 |
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(DE-627)NLEJ190390573 DE-627 ger DE-627 rakwb eng Stereochemistry of nitrogen heterocycles. 49. Synthesis and transformations of stereoisomeric 4-keto-2-methyl-n-chloro-trans-decahydroquinolines 1984 7 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Abstract Epimeric (with respect to the methyl group) stereoisomers of 4-keto-2-methyl-1-chloro-trans-decahydroquinoline were obtained, and their transformations under the influence of triethylamine were investigated. It was shown that the direction of the transformations depends on the steric orientation of the methyl group and the molar ratio of the N-chloroamine and triethylamine. The N-chloroamine isomer with an equatorial methyl group undergoes dehydrochlorination in the presence of excess triethylamine to give 2-methyl-4-hydroxy-trans-5,6,7,8,9,10-hexahydroquinoline. With an equimolar amount of triethylamine in solution in CCl4 the principal reaction pathway becomes dehydrochlorination and subsequent chlorination to give 2-methyl-4-hydroxy-3-chloro-trans-5,6,7,8,9,10-hexahydroquinoline. The N-chloroamine isomer with an axial methyl group in the presence of both excess and, in particular, equimolar amounts of triethylamine undergoes, in addition to dehydrochlorination and chlorination in the β position of the piperidine ring, cis-trans isomerization and subsequent dehydrogenation with the primary formation of 2-methyl-4-hydroxy-3-chloro-5,6,7,8-tetrahydroquinoline. The mechanism of the transformations is examined. Springer Online Journal Archives 1860-2002 Litvinenko, G. S. oth Voronenko, L. A. oth in Chemistry of heterocyclic compounds 1965 20(1984) vom: Juni, Seite 643-649 (DE-627)NLEJ188993940 (DE-600)2037128-7 1573-8353 nnns volume:20 year:1984 month:06 pages:643-649 extent:7 http://dx.doi.org/10.1007/BF00508674 GBV_USEFLAG_U ZDB-1-SOJ GBV_NL_ARTICLE AR 20 1984 6 643-649 7 |
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stereochemistry of nitrogen heterocycles. 49. synthesis and transformations of stereoisomeric 4-keto-2-methyl-n-chloro-trans-decahydroquinolines |
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Stereochemistry of nitrogen heterocycles. 49. Synthesis and transformations of stereoisomeric 4-keto-2-methyl-n-chloro-trans-decahydroquinolines |
| abstract |
Abstract Epimeric (with respect to the methyl group) stereoisomers of 4-keto-2-methyl-1-chloro-trans-decahydroquinoline were obtained, and their transformations under the influence of triethylamine were investigated. It was shown that the direction of the transformations depends on the steric orientation of the methyl group and the molar ratio of the N-chloroamine and triethylamine. The N-chloroamine isomer with an equatorial methyl group undergoes dehydrochlorination in the presence of excess triethylamine to give 2-methyl-4-hydroxy-trans-5,6,7,8,9,10-hexahydroquinoline. With an equimolar amount of triethylamine in solution in CCl4 the principal reaction pathway becomes dehydrochlorination and subsequent chlorination to give 2-methyl-4-hydroxy-3-chloro-trans-5,6,7,8,9,10-hexahydroquinoline. The N-chloroamine isomer with an axial methyl group in the presence of both excess and, in particular, equimolar amounts of triethylamine undergoes, in addition to dehydrochlorination and chlorination in the β position of the piperidine ring, cis-trans isomerization and subsequent dehydrogenation with the primary formation of 2-methyl-4-hydroxy-3-chloro-5,6,7,8-tetrahydroquinoline. The mechanism of the transformations is examined. |
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Abstract Epimeric (with respect to the methyl group) stereoisomers of 4-keto-2-methyl-1-chloro-trans-decahydroquinoline were obtained, and their transformations under the influence of triethylamine were investigated. It was shown that the direction of the transformations depends on the steric orientation of the methyl group and the molar ratio of the N-chloroamine and triethylamine. The N-chloroamine isomer with an equatorial methyl group undergoes dehydrochlorination in the presence of excess triethylamine to give 2-methyl-4-hydroxy-trans-5,6,7,8,9,10-hexahydroquinoline. With an equimolar amount of triethylamine in solution in CCl4 the principal reaction pathway becomes dehydrochlorination and subsequent chlorination to give 2-methyl-4-hydroxy-3-chloro-trans-5,6,7,8,9,10-hexahydroquinoline. The N-chloroamine isomer with an axial methyl group in the presence of both excess and, in particular, equimolar amounts of triethylamine undergoes, in addition to dehydrochlorination and chlorination in the β position of the piperidine ring, cis-trans isomerization and subsequent dehydrogenation with the primary formation of 2-methyl-4-hydroxy-3-chloro-5,6,7,8-tetrahydroquinoline. The mechanism of the transformations is examined. |
| abstract_unstemmed |
Abstract Epimeric (with respect to the methyl group) stereoisomers of 4-keto-2-methyl-1-chloro-trans-decahydroquinoline were obtained, and their transformations under the influence of triethylamine were investigated. It was shown that the direction of the transformations depends on the steric orientation of the methyl group and the molar ratio of the N-chloroamine and triethylamine. The N-chloroamine isomer with an equatorial methyl group undergoes dehydrochlorination in the presence of excess triethylamine to give 2-methyl-4-hydroxy-trans-5,6,7,8,9,10-hexahydroquinoline. With an equimolar amount of triethylamine in solution in CCl4 the principal reaction pathway becomes dehydrochlorination and subsequent chlorination to give 2-methyl-4-hydroxy-3-chloro-trans-5,6,7,8,9,10-hexahydroquinoline. The N-chloroamine isomer with an axial methyl group in the presence of both excess and, in particular, equimolar amounts of triethylamine undergoes, in addition to dehydrochlorination and chlorination in the β position of the piperidine ring, cis-trans isomerization and subsequent dehydrogenation with the primary formation of 2-methyl-4-hydroxy-3-chloro-5,6,7,8-tetrahydroquinoline. The mechanism of the transformations is examined. |
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<?xml version="1.0" encoding="UTF-8"?><collection xmlns="http://www.loc.gov/MARC21/slim"><record><leader>01000caa a22002652 4500</leader><controlfield tag="001">NLEJ190390573</controlfield><controlfield tag="003">DE-627</controlfield><controlfield tag="005">20230506081349.0</controlfield><controlfield tag="007">cr uuu---uuuuu</controlfield><controlfield tag="008">070525s1984 xx |||||o 00| ||eng c</controlfield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-627)NLEJ190390573</subfield></datafield><datafield tag="040" ind1=" " ind2=" "><subfield code="a">DE-627</subfield><subfield code="b">ger</subfield><subfield code="c">DE-627</subfield><subfield code="e">rakwb</subfield></datafield><datafield tag="041" ind1=" " ind2=" "><subfield code="a">eng</subfield></datafield><datafield tag="245" ind1="1" ind2="0"><subfield code="a">Stereochemistry of nitrogen heterocycles. 49. Synthesis and transformations of stereoisomeric 4-keto-2-methyl-n-chloro-trans-decahydroquinolines</subfield></datafield><datafield tag="264" ind1=" " ind2="1"><subfield code="c">1984</subfield></datafield><datafield tag="300" ind1=" " ind2=" "><subfield code="a">7</subfield></datafield><datafield tag="336" ind1=" " ind2=" "><subfield code="a">nicht spezifiziert</subfield><subfield code="b">zzz</subfield><subfield code="2">rdacontent</subfield></datafield><datafield tag="337" ind1=" " ind2=" "><subfield code="a">nicht spezifiziert</subfield><subfield code="b">z</subfield><subfield code="2">rdamedia</subfield></datafield><datafield tag="338" ind1=" " ind2=" "><subfield code="a">nicht spezifiziert</subfield><subfield code="b">zu</subfield><subfield code="2">rdacarrier</subfield></datafield><datafield tag="520" ind1=" " ind2=" "><subfield code="a">Abstract Epimeric (with respect to the methyl group) stereoisomers of 4-keto-2-methyl-1-chloro-trans-decahydroquinoline were obtained, and their transformations under the influence of triethylamine were investigated. It was shown that the direction of the transformations depends on the steric orientation of the methyl group and the molar ratio of the N-chloroamine and triethylamine. The N-chloroamine isomer with an equatorial methyl group undergoes dehydrochlorination in the presence of excess triethylamine to give 2-methyl-4-hydroxy-trans-5,6,7,8,9,10-hexahydroquinoline. With an equimolar amount of triethylamine in solution in CCl4 the principal reaction pathway becomes dehydrochlorination and subsequent chlorination to give 2-methyl-4-hydroxy-3-chloro-trans-5,6,7,8,9,10-hexahydroquinoline. The N-chloroamine isomer with an axial methyl group in the presence of both excess and, in particular, equimolar amounts of triethylamine undergoes, in addition to dehydrochlorination and chlorination in the β position of the piperidine ring, cis-trans isomerization and subsequent dehydrogenation with the primary formation of 2-methyl-4-hydroxy-3-chloro-5,6,7,8-tetrahydroquinoline. The mechanism of the transformations is examined.</subfield></datafield><datafield tag="533" ind1=" " ind2=" "><subfield code="f">Springer Online Journal Archives 1860-2002</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Litvinenko, G. S.</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Voronenko, L. A.</subfield><subfield code="4">oth</subfield></datafield><datafield tag="773" ind1="0" ind2="8"><subfield code="i">in</subfield><subfield code="t">Chemistry of heterocyclic compounds</subfield><subfield code="d">1965</subfield><subfield code="g">20(1984) vom: Juni, Seite 643-649</subfield><subfield code="w">(DE-627)NLEJ188993940</subfield><subfield code="w">(DE-600)2037128-7</subfield><subfield code="x">1573-8353</subfield><subfield code="7">nnns</subfield></datafield><datafield tag="773" ind1="1" ind2="8"><subfield code="g">volume:20</subfield><subfield code="g">year:1984</subfield><subfield code="g">month:06</subfield><subfield code="g">pages:643-649</subfield><subfield code="g">extent:7</subfield></datafield><datafield tag="856" ind1="4" ind2="0"><subfield code="u">http://dx.doi.org/10.1007/BF00508674</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_USEFLAG_U</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">ZDB-1-SOJ</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_NL_ARTICLE</subfield></datafield><datafield tag="951" ind1=" " ind2=" "><subfield code="a">AR</subfield></datafield><datafield tag="952" ind1=" " ind2=" "><subfield code="d">20</subfield><subfield code="j">1984</subfield><subfield code="c">6</subfield><subfield code="h">643-649</subfield><subfield code="g">7</subfield></datafield></record></collection>
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