Synthesis of azetidin-3-ones. Structure of N-tosyl-2-ethylazetidin-3-one
A one-step synthesis of azetidin-3-ones by intramolecular cyclization of 1-diazo-3-arenesulfamoylalkan-2-ones was developed. The yield of cyclic product increases to 70% in the presence of an alkyl or benzyl substituent in the hydrocarbon chain of the diazoketone. The structure of N-tosyl-2-ethylaze...
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| Veröffentlicht in: | Chem. Heterocycl. Compd. (Engl. Transl.); (United States) 1987-04, Vol.23 (4), p.390-395 |
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| container_title | Chem. Heterocycl. Compd. (Engl. Transl.); (United States) |
| container_volume | 23 |
| creator | Aliev, Z. G. Atovmyan, L. O. Sipyagin, A. M. Kartsev, V. G. Dobrokhotova, O. V. |
| description | A one-step synthesis of azetidin-3-ones by intramolecular cyclization of 1-diazo-3-arenesulfamoylalkan-2-ones was developed. The yield of cyclic product increases to 70% in the presence of an alkyl or benzyl substituent in the hydrocarbon chain of the diazoketone. The structure of N-tosyl-2-ethylazetidin-3-one was studied by x-ray diffraction analysis and it was shown that the four-membered ring has 15/sup 0/ inflection. IR spectra were recorded with a Specord 75 IR instrument in mineral oil. PMR spectra were recorded with Bruker WH-360 (360 MHz) and Jeol HL-60 (60 MHz) instruments in CDCl/sub 3/ solution, with TMS internal standard. UV spectra were obtained with a Specord UV-VIS instrument in methanol. |
| doi_str_mv | 10.1007/BF00546731 |
| format | Article |
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Structure of N-tosyl-2-ethylazetidin-3-one</title><source>SpringerLink Journals - AutoHoldings</source><creator>Aliev, Z. G. ; Atovmyan, L. O. ; Sipyagin, A. M. ; Kartsev, V. G. ; Dobrokhotova, O. V.</creator><creatorcontrib>Aliev, Z. G. ; Atovmyan, L. O. ; Sipyagin, A. M. ; Kartsev, V. G. ; Dobrokhotova, O. V. ; Institute of Chemical Physics, Chernogolovka (USSR)</creatorcontrib><description>A one-step synthesis of azetidin-3-ones by intramolecular cyclization of 1-diazo-3-arenesulfamoylalkan-2-ones was developed. The yield of cyclic product increases to 70% in the presence of an alkyl or benzyl substituent in the hydrocarbon chain of the diazoketone. The structure of N-tosyl-2-ethylazetidin-3-one was studied by x-ray diffraction analysis and it was shown that the four-membered ring has 15/sup 0/ inflection. IR spectra were recorded with a Specord 75 IR instrument in mineral oil. PMR spectra were recorded with Bruker WH-360 (360 MHz) and Jeol HL-60 (60 MHz) instruments in CDCl/sub 3/ solution, with TMS internal standard. UV spectra were obtained with a Specord UV-VIS instrument in methanol.</description><identifier>ISSN: 0009-3122</identifier><identifier>EISSN: 1573-8353</identifier><identifier>DOI: 10.1007/BF00546731</identifier><language>eng</language><publisher>United States</publisher><subject>400201 - Chemical & Physicochemical Properties ; 640302 - Atomic, Molecular & Chemical Physics- Atomic & Molecular Properties & Theory ; ATOMIC AND MOLECULAR PHYSICS ; CHEMICAL REACTION YIELD ; CHEMICAL REACTIONS ; CHEMICAL SHIFT ; CHLORINATED ALIPHATIC HYDROCARBONS ; CHLOROFORM ; COHERENT SCATTERING ; CONFIGURATION INTERACTION ; COUPLING ; COUPLING CONSTANTS ; DEHYDROCYCLIZATION ; DEUTERIUM COMPOUNDS ; DIFFRACTION ; ENERGY LEVELS ; EXCITED STATES ; HALOGENATED ALIPHATIC HYDROCARBONS ; HETEROCYCLIC COMPOUNDS ; HYDROGEN COMPOUNDS ; INFRARED SPECTRA ; INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY ; INTERMEDIATE COUPLING ; ISOMERIZATION ; ISOTOPE EFFECTS ; J-J COUPLING ; KETONES ; NMR SPECTRA ; ORGANIC CHLORINE COMPOUNDS ; ORGANIC COMPOUNDS ; ORGANIC HALOGEN COMPOUNDS ; ORGANIC NITROGEN COMPOUNDS ; ORGANIC SULFUR COMPOUNDS ; SCATTERING ; SPECTRA ; SYNTHESIS ; ULTRAVIOLET SPECTRA ; VIBRATIONAL STATES ; X-RAY DIFFRACTION ; YIELDS</subject><ispartof>Chem. 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V.</creatorcontrib><creatorcontrib>Institute of Chemical Physics, Chernogolovka (USSR)</creatorcontrib><title>Synthesis of azetidin-3-ones. Structure of N-tosyl-2-ethylazetidin-3-one</title><title>Chem. Heterocycl. Compd. (Engl. Transl.); (United States)</title><description>A one-step synthesis of azetidin-3-ones by intramolecular cyclization of 1-diazo-3-arenesulfamoylalkan-2-ones was developed. The yield of cyclic product increases to 70% in the presence of an alkyl or benzyl substituent in the hydrocarbon chain of the diazoketone. The structure of N-tosyl-2-ethylazetidin-3-one was studied by x-ray diffraction analysis and it was shown that the four-membered ring has 15/sup 0/ inflection. IR spectra were recorded with a Specord 75 IR instrument in mineral oil. PMR spectra were recorded with Bruker WH-360 (360 MHz) and Jeol HL-60 (60 MHz) instruments in CDCl/sub 3/ solution, with TMS internal standard. UV spectra were obtained with a Specord UV-VIS instrument in methanol.</description><subject>400201 - Chemical & Physicochemical Properties</subject><subject>640302 - Atomic, Molecular & Chemical Physics- Atomic & Molecular Properties & Theory</subject><subject>ATOMIC AND MOLECULAR PHYSICS</subject><subject>CHEMICAL REACTION YIELD</subject><subject>CHEMICAL REACTIONS</subject><subject>CHEMICAL SHIFT</subject><subject>CHLORINATED ALIPHATIC HYDROCARBONS</subject><subject>CHLOROFORM</subject><subject>COHERENT SCATTERING</subject><subject>CONFIGURATION INTERACTION</subject><subject>COUPLING</subject><subject>COUPLING CONSTANTS</subject><subject>DEHYDROCYCLIZATION</subject><subject>DEUTERIUM COMPOUNDS</subject><subject>DIFFRACTION</subject><subject>ENERGY LEVELS</subject><subject>EXCITED STATES</subject><subject>HALOGENATED ALIPHATIC HYDROCARBONS</subject><subject>HETEROCYCLIC COMPOUNDS</subject><subject>HYDROGEN COMPOUNDS</subject><subject>INFRARED SPECTRA</subject><subject>INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY</subject><subject>INTERMEDIATE COUPLING</subject><subject>ISOMERIZATION</subject><subject>ISOTOPE EFFECTS</subject><subject>J-J COUPLING</subject><subject>KETONES</subject><subject>NMR SPECTRA</subject><subject>ORGANIC CHLORINE COMPOUNDS</subject><subject>ORGANIC COMPOUNDS</subject><subject>ORGANIC HALOGEN COMPOUNDS</subject><subject>ORGANIC NITROGEN COMPOUNDS</subject><subject>ORGANIC SULFUR COMPOUNDS</subject><subject>SCATTERING</subject><subject>SPECTRA</subject><subject>SYNTHESIS</subject><subject>ULTRAVIOLET SPECTRA</subject><subject>VIBRATIONAL STATES</subject><subject>X-RAY DIFFRACTION</subject><subject>YIELDS</subject><issn>0009-3122</issn><issn>1573-8353</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1987</creationdate><recordtype>article</recordtype><recordid>eNpVkMFKxDAYhIMoWFcvPkHxKGT9kzRNctTFdYVFD6vnkCYprdRGkuyhPr1dVhBPw8x8zGEQuiawJADi7mENwKtaMHKCCsIFw5JxdooKAFCYEUrP0UVKH7MVRFYF2uymMXc-9akMbWm-fe5dP2KGw-jTstzluLd5H_2hfcE5pGnAFPvcTcN_-BKdtWZI_upXF-h9_fi22uDt69Pz6n6LLREsY0atMZVyjqtKttxYqQBkQySVwpLGN7IxhnPnpZtTYpva0hqgUspR4YCxBbo57oaUe51sn73tbBhHb7MWpFaM8xm6PUI2hpSib_VX7D9NnDQBfThK_x3FfgBQTFl1</recordid><startdate>198704</startdate><enddate>198704</enddate><creator>Aliev, Z. 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V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c173t-32caa49dd5948f5ac89008b18287c1beb8baa55de8d8b11cb6c2600499d27d033</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1987</creationdate><topic>400201 - Chemical & Physicochemical Properties</topic><topic>640302 - Atomic, Molecular & Chemical Physics- Atomic & Molecular Properties & Theory</topic><topic>ATOMIC AND MOLECULAR PHYSICS</topic><topic>CHEMICAL REACTION YIELD</topic><topic>CHEMICAL REACTIONS</topic><topic>CHEMICAL SHIFT</topic><topic>CHLORINATED ALIPHATIC HYDROCARBONS</topic><topic>CHLOROFORM</topic><topic>COHERENT SCATTERING</topic><topic>CONFIGURATION INTERACTION</topic><topic>COUPLING</topic><topic>COUPLING CONSTANTS</topic><topic>DEHYDROCYCLIZATION</topic><topic>DEUTERIUM COMPOUNDS</topic><topic>DIFFRACTION</topic><topic>ENERGY LEVELS</topic><topic>EXCITED STATES</topic><topic>HALOGENATED ALIPHATIC HYDROCARBONS</topic><topic>HETEROCYCLIC COMPOUNDS</topic><topic>HYDROGEN COMPOUNDS</topic><topic>INFRARED SPECTRA</topic><topic>INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY</topic><topic>INTERMEDIATE COUPLING</topic><topic>ISOMERIZATION</topic><topic>ISOTOPE EFFECTS</topic><topic>J-J COUPLING</topic><topic>KETONES</topic><topic>NMR SPECTRA</topic><topic>ORGANIC CHLORINE COMPOUNDS</topic><topic>ORGANIC COMPOUNDS</topic><topic>ORGANIC HALOGEN COMPOUNDS</topic><topic>ORGANIC NITROGEN COMPOUNDS</topic><topic>ORGANIC SULFUR COMPOUNDS</topic><topic>SCATTERING</topic><topic>SPECTRA</topic><topic>SYNTHESIS</topic><topic>ULTRAVIOLET SPECTRA</topic><topic>VIBRATIONAL STATES</topic><topic>X-RAY DIFFRACTION</topic><topic>YIELDS</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Aliev, Z. G.</creatorcontrib><creatorcontrib>Atovmyan, L. O.</creatorcontrib><creatorcontrib>Sipyagin, A. M.</creatorcontrib><creatorcontrib>Kartsev, V. G.</creatorcontrib><creatorcontrib>Dobrokhotova, O. V.</creatorcontrib><creatorcontrib>Institute of Chemical Physics, Chernogolovka (USSR)</creatorcontrib><collection>CrossRef</collection><collection>OSTI.GOV</collection><jtitle>Chem. Heterocycl. Compd. (Engl. Transl.); (United States)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Aliev, Z. G.</au><au>Atovmyan, L. O.</au><au>Sipyagin, A. M.</au><au>Kartsev, V. G.</au><au>Dobrokhotova, O. V.</au><aucorp>Institute of Chemical Physics, Chernogolovka (USSR)</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of azetidin-3-ones. Structure of N-tosyl-2-ethylazetidin-3-one</atitle><jtitle>Chem. Heterocycl. Compd. (Engl. Transl.); (United States)</jtitle><date>1987-04</date><risdate>1987</risdate><volume>23</volume><issue>4</issue><spage>390</spage><epage>395</epage><pages>390-395</pages><issn>0009-3122</issn><eissn>1573-8353</eissn><abstract>A one-step synthesis of azetidin-3-ones by intramolecular cyclization of 1-diazo-3-arenesulfamoylalkan-2-ones was developed. The yield of cyclic product increases to 70% in the presence of an alkyl or benzyl substituent in the hydrocarbon chain of the diazoketone. The structure of N-tosyl-2-ethylazetidin-3-one was studied by x-ray diffraction analysis and it was shown that the four-membered ring has 15/sup 0/ inflection. IR spectra were recorded with a Specord 75 IR instrument in mineral oil. PMR spectra were recorded with Bruker WH-360 (360 MHz) and Jeol HL-60 (60 MHz) instruments in CDCl/sub 3/ solution, with TMS internal standard. UV spectra were obtained with a Specord UV-VIS instrument in methanol.</abstract><cop>United States</cop><doi>10.1007/BF00546731</doi><tpages>6</tpages></addata></record> |
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| ispartof | Chem. Heterocycl. Compd. (Engl. Transl.); (United States), 1987-04, Vol.23 (4), p.390-395 |
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| source | SpringerLink Journals - AutoHoldings |
| subjects | 400201 - Chemical & Physicochemical Properties 640302 - Atomic, Molecular & Chemical Physics- Atomic & Molecular Properties & Theory ATOMIC AND MOLECULAR PHYSICS CHEMICAL REACTION YIELD CHEMICAL REACTIONS CHEMICAL SHIFT CHLORINATED ALIPHATIC HYDROCARBONS CHLOROFORM COHERENT SCATTERING CONFIGURATION INTERACTION COUPLING COUPLING CONSTANTS DEHYDROCYCLIZATION DEUTERIUM COMPOUNDS DIFFRACTION ENERGY LEVELS EXCITED STATES HALOGENATED ALIPHATIC HYDROCARBONS HETEROCYCLIC COMPOUNDS HYDROGEN COMPOUNDS INFRARED SPECTRA INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY INTERMEDIATE COUPLING ISOMERIZATION ISOTOPE EFFECTS J-J COUPLING KETONES NMR SPECTRA ORGANIC CHLORINE COMPOUNDS ORGANIC COMPOUNDS ORGANIC HALOGEN COMPOUNDS ORGANIC NITROGEN COMPOUNDS ORGANIC SULFUR COMPOUNDS SCATTERING SPECTRA SYNTHESIS ULTRAVIOLET SPECTRA VIBRATIONAL STATES X-RAY DIFFRACTION YIELDS |
| title | Synthesis of azetidin-3-ones. Structure of N-tosyl-2-ethylazetidin-3-one |
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