One-pot synthesis of bis-1,5,3-dithiazepanes from ethane-1,2-dithiol, formaldehyde, and ammonium salts
An efficient one-pot procedure has been developed for the synthesis of bis-1,5,3-dithiazepanes by reaction of ethane-1,2-dithiol with formaldehyde and ammonium salts. According to the X-ray diffraction data, the heterorings in 3,3′-[ethane-1,2-diylbis(sulfanediylmethanediyl)]bis(1,5,3-dithiazepane)...
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| Published in: | Russian journal of organic chemistry Vol. 49; no. 10; pp. 1542 - 1545 |
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| Format: | Journal Article |
| Language: | English |
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01-10-2013
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| Abstract | An efficient one-pot procedure has been developed for the synthesis of bis-1,5,3-dithiazepanes by reaction of ethane-1,2-dithiol with formaldehyde and ammonium salts. According to the X-ray diffraction data, the heterorings in 3,3′-[ethane-1,2-diylbis(sulfanediylmethanediyl)]bis(1,5,3-dithiazepane) in crystal adopt a
chair
conformation with axial orientation of the substituent on the nitrogen atom. |
|---|---|
| AbstractList | An efficient one-pot procedure has been developed for the synthesis of bis-1,5,3-dithiazepanes by reaction of ethane-1,2-dithiol with formaldehyde and ammonium salts. According to the X-ray diffraction data, the heterorings in 3,3′-[ethane-1,2-diylbis(sulfanediylmethanediyl)]bis(1,5,3-dithiazepane) in crystal adopt a
chair
conformation with axial orientation of the substituent on the nitrogen atom. |
| Author | Khabibullina, G. R. Akhmetova, V. R. Bushmarinov, I. S. Ibragimov, A. G. |
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| CitedBy_id | crossref_primary_10_1016_j_tet_2014_03_053 crossref_primary_10_1007_s11030_016_9656_0 crossref_primary_10_1007_s10593_022_03087_6 crossref_primary_10_1134_S1070428014110128 crossref_primary_10_1134_S1070428017020233 crossref_primary_10_1002_jhet_2344 crossref_primary_10_1134_S1070363216070124 crossref_primary_10_1002_chin_201416201 |
| Cites_doi | 10.1007/s11030-010-9248-3 10.1134/S1070428008020036 10.1248/cpb.27.1691 10.1016/j.tet.2007.08.104 10.1134/S1070428007060218 10.1016/j.tetlet.2012.05.161 10.1134/S1070428012040215 10.1021/ja00068a015 |
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| Keywords | Ammonium Salt Chair Conformation Aromatic Amine Dithiol Ammonium Fluoride |
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| References | MurzakovaNNProkof’evKITyumkinaTVIbragimovAGRuss. J. Org. Chem.20124858810.1134/S10704280120402151:CAS:528:DC%2BC38Xms1eitbg%3D AkhmetovaVRKhabibullinaGRRakhimovaEBVagapovRAKhairullinaRRNiatshinaZTMurzakovaNNMol. Diversity20101446310.1007/s11030-010-9248-31:CAS:528:DC%2BC3cXhsValsbbI SheldrickGMSHELXTL. Version 5. Software Reference Manual1994Madison, WISiemens Industrial Automation AkhmetovaVRNadyrgulovaGRTyumkinaTVStarikovaZAAntipinMYuKunakovaRVDzhemilevUMRuss. J. Org. Chem.20074391810.1134/S10704280070602181:CAS:528:DC%2BD2sXnslSgtLc%3D AkhmetovaVRNiatshinaZTKhabibullinaGRBushmarinovISBorisovaAOStarikovaZAKorzhovaLFKunakovaRVIzv. Akad. Nauk, Ser. Khim.2010980 AkhmetovaVRNadyrgulovaGRNiatshinaZTDzhemilevUMKhim. Geterotsikl. Soedin.20091443 PozharskiiAFSoldatenkovAKatritzkyARHeterocycles in Life and Society: An Introduction to Heterocyclic ChemistryBiochemistry and Applications20112nd edNew YorkWiley AlderRWHeilbronnerEHonneggerEMcEwenABMossREOlefirowiczEPethylloPASessionsRBWeismanGRWhiteJMYangZ-ZJ. Am. Chem. Soc.1993115658010.1021/ja00068a0151:CAS:528:DyaK3sXlsF2ns78%3D AkhmetovaVRNadyrgulovaGRTyumkinaTVStarikovaZAGolovanovDGAntipinMYuKunakovaRVDzhemilevUMIzv. Akad. Nauk, Ser. Khim.20061758 AkhmetovaVRVagapovRANadyrgulovaGRTyumkinaTVStarikovaZAAntipinMYKunakovaRVDzhemilevUMTetrahedron20076311 70210.1016/j.tet.2007.08.1041:CAS:528:DC%2BD2sXhtFOjurbM DronovVINigmatullinaRFKhalilovLMNikitinY EZh. Org. Khim.19791517091:CAS:528:DyaL3cXls1Kh RakhimovaEBEfremovaEABushmarinovISGoloveshkinASKhalilovLMIbragimovAGDzhemilevUMTetrahedron Lett.201253422510.1016/j.tetlet.2012.05.1611:CAS:528:DC%2BC38XptFCrs7k%3D ItoKSekiyaMChem. Pharm. Bull.197927169110.1248/cpb.27.16911:CAS:528:DyaL3cXktFCrtw%3D%3D RakhimovaEBVasil’evaIVKhalilovLMIbragimovAGDzhemilevUMKhim. Geterotsikl. Soedin.201271132 AkhmetovaVRKhairullinaRRNadyrgulovaGRKunakovaRVDzhemilevUMRuss. J. Org. Chem.20084419010.1134/S10704280080200361:CAS:528:DC%2BD1cXktFCqsL8%3D K Ito (483_CR9) 1979; 27 VR Akhmetova (483_CR6) 2008; 44 VR Akhmetova (483_CR4) 2006 EB Rakhimova (483_CR12) 2012; 7 EB Rakhimova (483_CR11) 2012; 53 VR Akhmetova (483_CR7) 2010 VR Akhmetova (483_CR13) 2007; 43 NN Murzakova (483_CR10) 2012; 48 VR Akhmetova (483_CR5) 2007; 63 GM Sheldrick (483_CR15) 1994 VI Dronov (483_CR8) 1979; 15 RW Alder (483_CR14) 1993; 115 AF Pozharskii (483_CR1) 2011 VR Akhmetova (483_CR2) 2009 VR Akhmetova (483_CR3) 2010; 14 |
| References_xml | – volume: 14 start-page: 463 year: 2010 ident: 483_CR3 publication-title: Mol. Diversity doi: 10.1007/s11030-010-9248-3 contributor: fullname: VR Akhmetova – volume: 44 start-page: 190 year: 2008 ident: 483_CR6 publication-title: Russ. J. Org. Chem. doi: 10.1134/S1070428008020036 contributor: fullname: VR Akhmetova – start-page: 1443 volume-title: Khim. Geterotsikl. Soedin. year: 2009 ident: 483_CR2 contributor: fullname: VR Akhmetova – volume: 27 start-page: 1691 year: 1979 ident: 483_CR9 publication-title: Chem. Pharm. Bull. doi: 10.1248/cpb.27.1691 contributor: fullname: K Ito – start-page: 1758 volume-title: Izv. Akad. Nauk, Ser. Khim. year: 2006 ident: 483_CR4 contributor: fullname: VR Akhmetova – volume: 7 start-page: 1132 year: 2012 ident: 483_CR12 publication-title: Khim. Geterotsikl. Soedin. contributor: fullname: EB Rakhimova – volume: 63 start-page: 11 702 year: 2007 ident: 483_CR5 publication-title: Tetrahedron doi: 10.1016/j.tet.2007.08.104 contributor: fullname: VR Akhmetova – volume-title: Biochemistry and Applications year: 2011 ident: 483_CR1 contributor: fullname: AF Pozharskii – start-page: 980 volume-title: Izv. Akad. Nauk, Ser. Khim. year: 2010 ident: 483_CR7 contributor: fullname: VR Akhmetova – volume: 43 start-page: 918 year: 2007 ident: 483_CR13 publication-title: Russ. J. Org. Chem. doi: 10.1134/S1070428007060218 contributor: fullname: VR Akhmetova – volume: 53 start-page: 4225 year: 2012 ident: 483_CR11 publication-title: Tetrahedron Lett. doi: 10.1016/j.tetlet.2012.05.161 contributor: fullname: EB Rakhimova – volume: 15 start-page: 1709 year: 1979 ident: 483_CR8 publication-title: Zh. Org. Khim. contributor: fullname: VI Dronov – volume-title: SHELXTL. Version 5. Software Reference Manual year: 1994 ident: 483_CR15 contributor: fullname: GM Sheldrick – volume: 48 start-page: 588 year: 2012 ident: 483_CR10 publication-title: Russ. J. Org. Chem. doi: 10.1134/S1070428012040215 contributor: fullname: NN Murzakova – volume: 115 start-page: 6580 year: 1993 ident: 483_CR14 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00068a015 contributor: fullname: RW Alder |
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| Snippet | An efficient one-pot procedure has been developed for the synthesis of bis-1,5,3-dithiazepanes by reaction of ethane-1,2-dithiol with formaldehyde and ammonium... |
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| Title | One-pot synthesis of bis-1,5,3-dithiazepanes from ethane-1,2-dithiol, formaldehyde, and ammonium salts |
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