Bicyclic Sultams with a Nitrogen at the Bridgehead and a Sulfur Atom in the Apex Position: Facile Preparation and Conformational Properties
A practical synthesis of bicyclic sultams with a pyramidal bridgehead nitrogen atom and a sulfur atom in the apex position has been elaborated. Compounds with 1‐azathiabicyclo[2.2.1]heptane (12a), ‐bicyclo[3.2.1]octane (12b, 12d), and ‐bicyclo[3.3.1]nonane (13b) skeletons were obtained by direct two...
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| Published in: | European Journal of Organic Chemistry Vol. 2010; no. 18; pp. 3481 - 3486 |
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01-06-2010
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| Abstract | A practical synthesis of bicyclic sultams with a pyramidal bridgehead nitrogen atom and a sulfur atom in the apex position has been elaborated. Compounds with 1‐azathiabicyclo[2.2.1]heptane (12a), ‐bicyclo[3.2.1]octane (12b, 12d), and ‐bicyclo[3.3.1]nonane (13b) skeletons were obtained by direct twofold inter/intramolecular alkylation of corresponding monocyclic sultams 9 and 10 with α,ω‐dihalides 11 in K2CO3/DMF in 56, 68, 52 and 52 % yield, respectively. On the other hand, a 1‐aza‐9‐thiabicyclo[4.2.1]nonane derivative (12c) could be prepared only by stepwise dialkylation in 24 % overall yield. Structural and conformational properties of four of the newly prepared bicyclic sultams in solution as well as in the solid state are discussed.
Bicyclic sultams with 1‐azathiabicyclo[2.2.1]heptane, ‐bicyclo[3.2.1]octane, and‐bicyclo[3.3.1]nonane skeletons have been prepared by direct twofold inter/intramolecular alkylation of corresponding monocyclic sultams with α,ω‐dihalides in 56, 68, 52 and 52 % yield. |
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| AbstractList | A practical synthesis of bicyclic sultams with a pyramidal bridgehead nitrogen atom and a sulfur atom in the apex position has been elaborated. Compounds with 1‐azathiabicyclo[2.2.1]heptane (
12a
), ‐bicyclo[3.2.1]octane (
12b
,
12d
), and ‐bicyclo[3.3.1]nonane (
13b
) skeletons were obtained by direct twofold inter/intramolecular alkylation of corresponding monocyclic sultams
9
and
10
with α,ω‐dihalides
11
in K
2
CO
3
/DMF in 56, 68, 52 and 52 % yield, respectively. On the other hand, a 1‐aza‐9‐thiabicyclo[4.2.1]nonane derivative (
12c
) could be prepared only by stepwise dialkylation in 24 % overall yield. Structural and conformational properties of four of the newly prepared bicyclic sultams in solution as well as in the solid state are discussed. A practical synthesis of bicyclic sultams with a pyramidal bridgehead nitrogen atom and a sulfur atom in the apex position has been elaborated. Compounds with 1‐azathiabicyclo[2.2.1]heptane (12a), ‐bicyclo[3.2.1]octane (12b, 12d), and ‐bicyclo[3.3.1]nonane (13b) skeletons were obtained by direct twofold inter/intramolecular alkylation of corresponding monocyclic sultams 9 and 10 with α,ω‐dihalides 11 in K2CO3/DMF in 56, 68, 52 and 52 % yield, respectively. On the other hand, a 1‐aza‐9‐thiabicyclo[4.2.1]nonane derivative (12c) could be prepared only by stepwise dialkylation in 24 % overall yield. Structural and conformational properties of four of the newly prepared bicyclic sultams in solution as well as in the solid state are discussed. Bicyclic sultams with 1‐azathiabicyclo[2.2.1]heptane, ‐bicyclo[3.2.1]octane, and‐bicyclo[3.3.1]nonane skeletons have been prepared by direct twofold inter/intramolecular alkylation of corresponding monocyclic sultams with α,ω‐dihalides in 56, 68, 52 and 52 % yield. |
| Author | Rassadin, Valentin A. Sokolov, Viktor V. Yufit, Dmitry S. de Meijere, Armin Tomashevskiy, Aleksandr A. Kozhushkov, Sergei I. Grosheva, Daria S. |
| Author_xml | – sequence: 1 givenname: Valentin A. surname: Rassadin fullname: Rassadin, Valentin A. organization: Department of Chemistry, Saint Petersburg State University, Universitetskii pr. 26, 198504 Saint Petersburg, Russia – sequence: 2 givenname: Daria S. surname: Grosheva fullname: Grosheva, Daria S. organization: Department of Chemistry, Saint Petersburg State University, Universitetskii pr. 26, 198504 Saint Petersburg, Russia – sequence: 3 givenname: Aleksandr A. surname: Tomashevskiy fullname: Tomashevskiy, Aleksandr A. organization: Department of Chemistry, Saint Petersburg State University, Universitetskii pr. 26, 198504 Saint Petersburg, Russia – sequence: 4 givenname: Viktor V. surname: Sokolov fullname: Sokolov, Viktor V. email: vsokolo@mail.ru organization: Department of Chemistry, Saint Petersburg State University, Universitetskii pr. 26, 198504 Saint Petersburg, Russia – sequence: 5 givenname: Dmitry S. surname: Yufit fullname: Yufit, Dmitry S. organization: Department of Chemistry, University of Durham, South Rd., Durham DH1 3LE, UK – sequence: 6 givenname: Sergei I. surname: Kozhushkov fullname: Kozhushkov, Sergei I. organization: Institut für Organische und Biomolekulare Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, Germany – sequence: 7 givenname: Armin surname: de Meijere fullname: de Meijere, Armin email: ameijer1@gwdg.de organization: Institut für Organische und Biomolekulare Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, Germany |
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| Cites_doi | 10.1021/ja992161c 10.1021/jm9906015 10.1021/ja00095a010 10.1002/ange.200351102 10.1016/j.bmcl.2007.07.002 10.1021/ja00063a008 10.1021/ja994293b 10.1016/S0040-4020(01)97102-9 10.1021/jo0611162 10.1002/ejoc.200900113 10.1016/j.bmcl.2005.11.015 10.1021/bi00044a011 10.1016/j.bmcl.2006.10.079 10.1021/ol049679s 10.1107/S0108270195011796 10.1080/00397917709409277 10.1021/ol0480123 |
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| References_xml | – start-page: 605 year: 2008 end-page: 617 publication-title: Khim. Geterotsykl. Soed. – volume: 343 start-page: 198 year: 1995 end-page: 201 publication-title: Dokl. Akad. Nauk – volume: 7 start-page: 43 year: 2005 end-page: 46 publication-title: Org. Lett. – volume: 116 start-page: 7081 year: 1994 end-page: 7087 publication-title: J. Am. Chem. Soc. – volume: 30 start-page: 2345 year: 1974 end-page: 2352 publication-title: Tetrahedron – volume: 7 start-page: 559 year: 1977 end-page: 568 publication-title: Synth. Commun. – volume: 16 start-page: 854 year: 2006 end-page: 858 publication-title: Bioorg. Med. Chem. Lett. – start-page: 2635 year: 2009 end-page: 2641 publication-title: Eur. J. Org. Chem. – volume: 115 start-page: 3901 year: 1993 end-page: 3908 publication-title: J. Am. Chem. Soc. – volume: 17 start-page: 5465 year: 2007 end-page: 5471 publication-title: Bioorg. Med. Chem. Lett. – volume: 17 start-page: 736 year: 2007 end-page: 740 publication-title: Bioorg. Med. Chem. Lett. – volume: 71 start-page: 6573 year: 2006 end-page: 6578 publication-title: J. Org. Chem. – volume: 121 start-page: 8126 year: 1999 end-page: 8127 publication-title: J. Am. Chem. Soc. – volume: 6 start-page: 1313 year: 2004 end-page: 1315 publication-title: Org. Lett. – volume: 43 start-page: 2040 year: 2000 end-page: 2048 publication-title: J. Med. Chem. – volume: 285 start-page: 118 year: 1985 end-page: 120 publication-title: Dokl. Akad. Nauk SSSR – volume: 34 start-page: 14344 year: 1995 end-page: 14355 publication-title: Biochemistry – volume: 112 start-page: 3375 year: 2000 end-page: 3385 publication-title: J. Am. Chem. Soc. – volume: 115 start-page: 2724 year: 2003 end-page: 2727 publication-title: Angew. Chem. – volume: 52 start-page: 469 year: 1996 end-page: 470 publication-title: Acta Crystallogr., Sect. C – ident: e_1_2_6_10_2 doi: 10.1021/ja992161c – ident: e_1_2_6_19_2 – start-page: 605 year: 2008 ident: e_1_2_6_12_2 publication-title: Khim. Geterotsykl. Soed. contributor: fullname: Rassadin V. A. – ident: e_1_2_6_3_2 doi: 10.1021/jm9906015 – ident: e_1_2_6_16_2 doi: 10.1021/ja00095a010 – ident: e_1_2_6_20_2 doi: 10.1002/ange.200351102 – ident: e_1_2_6_4_2 doi: 10.1016/j.bmcl.2007.07.002 – ident: e_1_2_6_17_2 doi: 10.1021/ja00063a008 – ident: e_1_2_6_6_2 doi: 10.1021/ja994293b – ident: e_1_2_6_15_2 – ident: e_1_2_6_23_2 doi: 10.1016/S0040-4020(01)97102-9 – ident: e_1_2_6_9_2 doi: 10.1021/jo0611162 – ident: e_1_2_6_13_2 doi: 10.1002/ejoc.200900113 – ident: e_1_2_6_2_2 doi: 10.1016/j.bmcl.2005.11.015 – ident: e_1_2_6_7_2 doi: 10.1021/bi00044a011 – ident: e_1_2_6_5_2 doi: 10.1016/j.bmcl.2006.10.079 – ident: e_1_2_6_18_2 – ident: e_1_2_6_8_2 doi: 10.1021/ol049679s – volume: 285 start-page: 118 year: 1985 ident: e_1_2_6_24_2 publication-title: Dokl. Akad. Nauk SSSR contributor: fullname: Levina O. I. – ident: e_1_2_6_21_2 doi: 10.1107/S0108270195011796 – ident: e_1_2_6_14_2 doi: 10.1080/00397917709409277 – ident: e_1_2_6_22_2 – ident: e_1_2_6_1_2 – ident: e_1_2_6_11_2 doi: 10.1021/ol0480123 – volume: 343 start-page: 198 year: 1995 ident: e_1_2_6_25_2 publication-title: Dokl. Akad. Nauk contributor: fullname: Zefirov N. S. |
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| SubjectTerms | Bridged sultams Conformational analysis Cyclization Oxidative deprotection Solid-state structures |
| Title | Bicyclic Sultams with a Nitrogen at the Bridgehead and a Sulfur Atom in the Apex Position: Facile Preparation and Conformational Properties |
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