Practical Synthesis of N‑Substituted Cyanamides via Tiemann Rearrangement of Amidoximes
A facile and general synthesis of various N-substituted cyanamides was accomplished by the Tiemann rearrangement of amidoximes with benzenesulfonyl chlorides (TsCl or o-NsCl) and DIPEA.
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| Published in | Organic letters Vol. 16; no. 3; pp. 892 - 895 |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
07.02.2014
Amer Chemical Soc |
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| Abstract | A facile and general synthesis of various N-substituted cyanamides was accomplished by the Tiemann rearrangement of amidoximes with benzenesulfonyl chlorides (TsCl or o-NsCl) and DIPEA. |
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| AbstractList | A facile and general synthesis of various N-substituted cyanamides was accomplished by the Tiemann rearrangement of amidoximes with benzenesulfonyl chlorides (TsCl or o-NsCl) and DIPEA. |
| Author | Hsieh, Tsung-Han Liao, Pen-Yuan Chien, Tun-Cheng Shih, Yu-Chiao Liao, Zhen-Yuan Lin, Chia-Chi Chang, Chih-Wei Yeh, Wen-Hsiung |
| AuthorAffiliation | Department of Chemistry National Taiwan Normal University |
| AuthorAffiliation_xml | – name: Department of Chemistry – name: National Taiwan Normal University |
| Author_xml | – sequence: 1 givenname: Chia-Chi surname: Lin fullname: Lin, Chia-Chi – sequence: 2 givenname: Tsung-Han surname: Hsieh fullname: Hsieh, Tsung-Han – sequence: 3 givenname: Pen-Yuan surname: Liao fullname: Liao, Pen-Yuan – sequence: 4 givenname: Zhen-Yuan surname: Liao fullname: Liao, Zhen-Yuan – sequence: 5 givenname: Chih-Wei surname: Chang fullname: Chang, Chih-Wei – sequence: 6 givenname: Yu-Chiao surname: Shih fullname: Shih, Yu-Chiao – sequence: 7 givenname: Wen-Hsiung surname: Yeh fullname: Yeh, Wen-Hsiung – sequence: 8 givenname: Tun-Cheng surname: Chien fullname: Chien, Tun-Cheng email: tcchien@ntnu.edu.tw |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/24423009$$D View this record in MEDLINE/PubMed |
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| Keywords | ARYL ONE-POT SYNTHESIS RHODIUM-CATALYZED CYANATION PHENYL-P-TOLUENESULFONAMIDE CARBODIIMIDES |
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| References | DAMRAUER, R (WOS:A1980JL01500032) 1980; 45 Anbarasan, P (WOS:000290101500020) 2011; 17 Cioffi, CL (WOS:000284080300056) 2010; 75 Yang, Y (WOS:000295817100050) 2011; 13 Gerfaud, T (WOS:000297274700010) 2011; 13 RICHTER, R (WOS:A1983QR51700022) 1983; 48 Yamamoto, Y (WOS:000269967500012) 2009; 50 GARAPON, J (WOS:A1970H838500014) 1970 Nekrasov, DD (WOS:000225846300001) 2004; 40 Bakunov, SA (WOS:000088247900018) 2000 Tam, A (WOS:000322210600026) 2013; 15 Tiemann, F. (000331163900064.21) 1891; 24 BAKUNOV, SA (WOS:A1994PG23200018) 1994 BOYER, JH (WOS:A1970G799700091) 1970; 35 PARTRIDGE, MW (WOS:A1958WK67500005) 1958 Kloeckner, U (WOS:000298411700016) 2012; 23 Gong, TJ (WOS:000322432400013) 2013; 135 Chaitanya, M (WOS:000326320200012) 2013; 15 Crutchley, RJ (WOS:000171343600007) 2001; 219 Anbarasan, P (WOS:000286729300034) 2011; 50 Larraufie, MH (WOS:000303104500001) 2012; 44 DONDONI, A (WOS:A1977DX45400011) 1977; 42 PARTRIDGE, MW (WOS:A1953YE01900004) 1953; 5 Yamamoto, Y (WOS:000253170200033) 2008; 49 ULRICH, H (WOS:A1978EV56700013) 1978; 43 Garapon J. (ref13/cit13) 1970; 11 Bakunov S. A. (ref10/cit10) 1994 Yang Y. (ref3/cit3c) 2011; 13 Tam A. (ref14/cit14) 2013; 15 Yamamoto Y. (ref9/cit9) 2009; 50 Partridge M. W. (ref6/cit6) 1953; 5 Bakunov S. A. (ref7/cit7) 2000 Chaitanya M. (ref3/cit3b) 2013; 15 Partridge M. W. (ref16/cit16) 1958 Kloeckner U. (ref17/cit17a) 2012; 23 Anbarasan P. (ref3/cit3e) 2011; 50 Damrauer R. (ref11/cit11b) 1980; 45 Yamamoto Y. (ref15/cit15) 2008; 49 Anbarasan P. (ref3/cit3d) 2011; 17 Crutchley R. J. (ref4/cit4) 2001; 219 Boyer J. H. (ref12/cit12b) 1970; 35 Gong T.-J. (ref3/cit3a) 2013; 135 Richter R. (ref11/cit11a) 1983; 48 Ulrich H. (ref8/cit8) 1978; 43 Larraufie M. H. (ref1/cit1) 2012; 44 Nekrasov D. D. (ref2/cit2) 2004; 40 Tiemann F. (ref5/cit5) 1891; 24 Dondoni A. (ref12/cit12a) 1977; 42 Gerfaud T. (ref18/cit18) 2011; 13 Cioffi C. L. (ref17/cit17b) 2010; 75 |
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| Snippet | A facile and general synthesis of various N-substituted cyanamides was accomplished by the Tiemann rearrangement of amidoximes with benzenesulfonyl chlorides... |
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| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | Practical Synthesis of N‑Substituted Cyanamides via Tiemann Rearrangement of Amidoximes |
| URI | http://dx.doi.org/10.1021/ol403645y http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000331163900064 https://www.ncbi.nlm.nih.gov/pubmed/24423009 https://search.proquest.com/docview/1499126234 |
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