Convenient one-pot access to 2H-3-nitrothiochromenes from 2-bromobenzaldehydes, sodium sulfide and beta-nitrostyrenes
An efficient synthesis of 2H-3-nitrothiochromenes via a cascade reaction was established. Starting from commercially available o-bromobenzaldehydes and beta-nitrostyrenes with sodium sulfide nonahydrate as an inexpensive sulfur source, various substituted thiochromenes were synthesized with high fun...
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| Published in | Organic & biomolecular chemistry Vol. 17; no. 26; pp. 6355 - 6358 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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Royal Soc Chemistry
14.07.2019
Royal Society of Chemistry |
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| Abstract | An efficient synthesis of 2H-3-nitrothiochromenes via a cascade reaction was established. Starting from commercially available o-bromobenzaldehydes and beta-nitrostyrenes with sodium sulfide nonahydrate as an inexpensive sulfur source, various substituted thiochromenes were synthesized with high functional group tolerance without any added transition metal catalyst or additive. |
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| AbstractList | An efficient synthesis of 2H-3-nitrothiochromenes via a cascade reaction was established. Starting from commercially available o-bromobenzaldehydes and β-nitrostyrenes with sodium sulfide nonahydrate as an inexpensive sulfur source, various substituted thiochromenes were synthesized with high functional group tolerance without any added transition metal catalyst or additive. An efficient synthesis of 2H-3-nitrothiochromenes via a cascade reaction was established. Starting from commercially available o-bromobenzaldehydes and beta-nitrostyrenes with sodium sulfide nonahydrate as an inexpensive sulfur source, various substituted thiochromenes were synthesized with high functional group tolerance without any added transition metal catalyst or additive. |
| Author | Youhei, Chitose Thanh Binh Nguyen Thi Thu Huong Le Quy Hien Le Dinh Hung Mac |
| Author_xml | – sequence: 1 surname: Thi Thu Huong Le fullname: Thi Thu Huong Le organization: VNU Univ Sci, Fac Chem, Med Chem Lab, 19 Le Thanh Thng, Hanoi, Vietnam – sequence: 2 givenname: Chitose surname: Youhei fullname: Youhei, Chitose organization: VNU Univ Sci, Fac Chem, Med Chem Lab, 19 Le Thanh Thng, Hanoi, Vietnam – sequence: 3 surname: Quy Hien Le fullname: Quy Hien Le organization: VNU Univ Sci, Fac Chem, Med Chem Lab, 19 Le Thanh Thng, Hanoi, Vietnam – sequence: 4 surname: Thanh Binh Nguyen fullname: Thanh Binh Nguyen email: nguyen@icsn.cnrs-gif.fr organization: Univ Paris Saclay, Univ Paris Sud, Inst Chim Subst Nat, CNRS UPR 2301, 1 Ave Terrasse, F-91198 Gif Sur Yvette, France – sequence: 5 surname: Dinh Hung Mac fullname: Dinh Hung Mac email: macdinhhung@hus.edu.vn organization: VNU Univ Sci, Fac Chem, Med Chem Lab, 19 Le Thanh Thng, Hanoi, Vietnam |
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| Cites_doi | 10.1016/j.tetlet.2014.08.037 10.1021/ol500361w 10.1021/jm049782n 10.1021/acs.joc.6b02740 10.1055/s-0036-1588377 10.1016/j.bmc.2004.09.038 10.1002/adsc.200700331 10.1016/j.bmcl.2006.04.090 10.1002/adsc.200700158 10.1016/j.tetlet.2008.01.113 10.1021/acs.joc.7b00579 10.1021/cr8004229 10.1021/ol060065s 10.1002/adsc.201300281 10.1021/ja063328m 10.1002/chem.201103525 10.1021/ol401944a 10.1002/adsc.200700407 10.1021/jm011066n 10.3762/bjoc.8.191 10.1021/acs.orglett.6b01639 10.1002/ejoc.201501618 10.1021/acs.jmedchem.5b00991 10.1021/cr500235v 10.1021/jm0000113 10.1021/ja0491477 |
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| Keywords | DESIGN ENANTIOSELECTIVE SYNTHESIS ANALOGS THIOCHROMENES |
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| SubjectTerms | Cascade chemical reactions Chemistry Chemistry, Organic Crystallography Functional groups Physical Sciences Science & Technology Sodium Sodium sulfide Sulfide Sulfides Sulfur Transition metals |
| Title | Convenient one-pot access to 2H-3-nitrothiochromenes from 2-bromobenzaldehydes, sodium sulfide and beta-nitrostyrenes |
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