Transformations of 2-[(Methoxy-2-oxoethyl)sulfanyl]-5,6-dihydropyridine under Acid Catalysis: Unexpected Transition to Derivatives of 5,6-Dihydropyridin-2(1H)-one and 2,3,6,7-Tetrahydro-5H-[1,3]thiazolo[3,2-a]pyridine
Derivatives of 2,3,6,7-tetrahydro-5 H -[1,3]thiazolo[3,2- a ]pyridine and 5,6-dihydropyridin-2(1 H )-one were unexpectedly obtained at treating methyl 2-[(6-methyl-3-ethoxy-5,6-dihydropyridin-2-yl)sulfanyl]-acetate with a dilute solution of hydrochloric acid. Their formation resulted from the hydrat...
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| Veröffentlicht in: | Russian journal of organic chemistry 2018-05, Vol.54 (5), p.691-695 |
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| container_title | Russian journal of organic chemistry |
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| creator | Nedolya, N. A. Tarasova, O. A. Albanov, A. I. Trofimov, B. A. |
| description | Derivatives of 2,3,6,7-tetrahydro-5
H
-[1,3]thiazolo[3,2-
a
]pyridine and 5,6-dihydropyridin-2(1
H
)-one were unexpectedly obtained at treating methyl 2-[(6-methyl-3-ethoxy-5,6-dihydropyridin-2-yl)sulfanyl]-acetate with a dilute solution of hydrochloric acid. Their formation resulted from the hydration of 5,6-dihydropyridine at the C=N bond accompanied with the elimination of a methyl 2-sulfanylacetate molecule and the addition of the methyl 2-sulfanylacetate to the second 5,6-dihydropyridine molecule at the C
3
=C
4
bond followed by the elimination of a methanol molecule and the closure of a thiazole ring. |
| doi_str_mv | 10.1134/S1070428018050032 |
| format | Article |
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H
-[1,3]thiazolo[3,2-
a
]pyridine and 5,6-dihydropyridin-2(1
H
)-one were unexpectedly obtained at treating methyl 2-[(6-methyl-3-ethoxy-5,6-dihydropyridin-2-yl)sulfanyl]-acetate with a dilute solution of hydrochloric acid. Their formation resulted from the hydration of 5,6-dihydropyridine at the C=N bond accompanied with the elimination of a methyl 2-sulfanylacetate molecule and the addition of the methyl 2-sulfanylacetate to the second 5,6-dihydropyridine molecule at the C
3
=C
4
bond followed by the elimination of a methanol molecule and the closure of a thiazole ring.</description><identifier>ISSN: 1070-4280</identifier><identifier>EISSN: 1608-3393</identifier><identifier>DOI: 10.1134/S1070428018050032</identifier><language>eng</language><publisher>Moscow: Pleiades Publishing</publisher><subject>Catalysis ; Chemistry ; Chemistry and Materials Science ; Derivatives ; Dilution ; Hydrochloric acid ; Molecular chains ; Organic Chemistry</subject><ispartof>Russian journal of organic chemistry, 2018-05, Vol.54 (5), p.691-695</ispartof><rights>Pleiades Publishing, Ltd. 2018</rights><rights>Copyright Springer Science & Business Media 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c316t-4c4d94f0ed9fb80545edbc4aacbca4b8ca2f27fc19df9588304cff33871406c33</citedby><cites>FETCH-LOGICAL-c316t-4c4d94f0ed9fb80545edbc4aacbca4b8ca2f27fc19df9588304cff33871406c33</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1134/S1070428018050032$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1134/S1070428018050032$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27924,27925,41488,42557,51319</link.rule.ids></links><search><creatorcontrib>Nedolya, N. A.</creatorcontrib><creatorcontrib>Tarasova, O. A.</creatorcontrib><creatorcontrib>Albanov, A. I.</creatorcontrib><creatorcontrib>Trofimov, B. A.</creatorcontrib><title>Transformations of 2-[(Methoxy-2-oxoethyl)sulfanyl]-5,6-dihydropyridine under Acid Catalysis: Unexpected Transition to Derivatives of 5,6-Dihydropyridin-2(1H)-one and 2,3,6,7-Tetrahydro-5H-[1,3]thiazolo[3,2-a]pyridine</title><title>Russian journal of organic chemistry</title><addtitle>Russ J Org Chem</addtitle><description>Derivatives of 2,3,6,7-tetrahydro-5
H
-[1,3]thiazolo[3,2-
a
]pyridine and 5,6-dihydropyridin-2(1
H
)-one were unexpectedly obtained at treating methyl 2-[(6-methyl-3-ethoxy-5,6-dihydropyridin-2-yl)sulfanyl]-acetate with a dilute solution of hydrochloric acid. Their formation resulted from the hydration of 5,6-dihydropyridine at the C=N bond accompanied with the elimination of a methyl 2-sulfanylacetate molecule and the addition of the methyl 2-sulfanylacetate to the second 5,6-dihydropyridine molecule at the C
3
=C
4
bond followed by the elimination of a methanol molecule and the closure of a thiazole ring.</description><subject>Catalysis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Derivatives</subject><subject>Dilution</subject><subject>Hydrochloric acid</subject><subject>Molecular chains</subject><subject>Organic Chemistry</subject><issn>1070-4280</issn><issn>1608-3393</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNp1kd1uEzEQhVcIJErhAbizxE0rrWH8s7te7qoUCFIRF6RXUbRy_ENcbe1gO1WWN-VtcBIQQoirGWnOOd9opqpeEnhNCONvvhDogFMBREADwOij6oy0IDBjPXtc-jLGh_nT6llKdwDACWdn1Y9FlD7ZEO9ldsEnFCyieHnxyeRN2E-Y4rAPpZ_Gy7QbrfTTuMJN3WLtNpOOYTtFp503aOe1iehKOY1mMstxSi69Rbfe7LdGZaPREeQOEJQDujbRPRTkgzkiD4nXfyViekHmlziUaOk1ojWr27rDC5OjPOpwM8dLUrNV3jj5PYxhyWqK5er3Rs-rJ1aOybz4Vc-r2_fvFrM5vvn84ePs6gYrRtqMueK65xaM7u263I43Rq8Vl1KtleRroSS1tLOK9Nr2jRAMuLKWMdERDq1i7Lx6dcrdxvBtZ1Ie7sIu-oIcKLREdAxAFBU5qVQMKUVjh2109zJOA4Hh8MHhnw8WDz15UtH6ryb-Sf6_6Scw1Z7b</recordid><startdate>20180501</startdate><enddate>20180501</enddate><creator>Nedolya, N. A.</creator><creator>Tarasova, O. A.</creator><creator>Albanov, A. I.</creator><creator>Trofimov, B. A.</creator><general>Pleiades Publishing</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20180501</creationdate><title>Transformations of 2-[(Methoxy-2-oxoethyl)sulfanyl]-5,6-dihydropyridine under Acid Catalysis: Unexpected Transition to Derivatives of 5,6-Dihydropyridin-2(1H)-one and 2,3,6,7-Tetrahydro-5H-[1,3]thiazolo[3,2-a]pyridine</title><author>Nedolya, N. A. ; Tarasova, O. A. ; Albanov, A. I. ; Trofimov, B. A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c316t-4c4d94f0ed9fb80545edbc4aacbca4b8ca2f27fc19df9588304cff33871406c33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Catalysis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Derivatives</topic><topic>Dilution</topic><topic>Hydrochloric acid</topic><topic>Molecular chains</topic><topic>Organic Chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nedolya, N. A.</creatorcontrib><creatorcontrib>Tarasova, O. A.</creatorcontrib><creatorcontrib>Albanov, A. I.</creatorcontrib><creatorcontrib>Trofimov, B. A.</creatorcontrib><collection>CrossRef</collection><jtitle>Russian journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nedolya, N. A.</au><au>Tarasova, O. A.</au><au>Albanov, A. I.</au><au>Trofimov, B. A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Transformations of 2-[(Methoxy-2-oxoethyl)sulfanyl]-5,6-dihydropyridine under Acid Catalysis: Unexpected Transition to Derivatives of 5,6-Dihydropyridin-2(1H)-one and 2,3,6,7-Tetrahydro-5H-[1,3]thiazolo[3,2-a]pyridine</atitle><jtitle>Russian journal of organic chemistry</jtitle><stitle>Russ J Org Chem</stitle><date>2018-05-01</date><risdate>2018</risdate><volume>54</volume><issue>5</issue><spage>691</spage><epage>695</epage><pages>691-695</pages><issn>1070-4280</issn><eissn>1608-3393</eissn><abstract>Derivatives of 2,3,6,7-tetrahydro-5
H
-[1,3]thiazolo[3,2-
a
]pyridine and 5,6-dihydropyridin-2(1
H
)-one were unexpectedly obtained at treating methyl 2-[(6-methyl-3-ethoxy-5,6-dihydropyridin-2-yl)sulfanyl]-acetate with a dilute solution of hydrochloric acid. Their formation resulted from the hydration of 5,6-dihydropyridine at the C=N bond accompanied with the elimination of a methyl 2-sulfanylacetate molecule and the addition of the methyl 2-sulfanylacetate to the second 5,6-dihydropyridine molecule at the C
3
=C
4
bond followed by the elimination of a methanol molecule and the closure of a thiazole ring.</abstract><cop>Moscow</cop><pub>Pleiades Publishing</pub><doi>10.1134/S1070428018050032</doi><tpages>5</tpages></addata></record> |
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| subjects | Catalysis Chemistry Chemistry and Materials Science Derivatives Dilution Hydrochloric acid Molecular chains Organic Chemistry |
| title | Transformations of 2-[(Methoxy-2-oxoethyl)sulfanyl]-5,6-dihydropyridine under Acid Catalysis: Unexpected Transition to Derivatives of 5,6-Dihydropyridin-2(1H)-one and 2,3,6,7-Tetrahydro-5H-[1,3]thiazolo[3,2-a]pyridine |
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