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Literature DB >> 28922917

Diverting Reactive Intermediates Toward Unusual Chemistry: Unexpected Anthranil Products from Davis-Beirut Reaction.

Jie S Zhu¹, Jung-Ho Son¹, Andrew P Teuthorn¹, Makhluf J Haddadin², Mark J Kurth¹, Dean J Tantillo¹.

Abstract

The discovery of a new variation on the Davis-Beirut reaction is described in which an atypical heterocyclic framework (the anthranil or benzo[c]isoxazole framework) is formed as the result of diversion of a key reactive intermediate away from its expected reactivity-a potentially general approach to reaction design and development. Experimental and computational support for the proposed mechanism and origins of altered reactivity are described.

Entities: Chemical Disease Species

Mesh：

Substances：
Isoxazoles
anthranil

Year: 2017 PMID： 28922917 PMCID： PMC5897912 DOI： 10.1021/acs.joc.7b01521

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

41 in total

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6. Pericyclic cascade with chirality transfer: reaction pathway and origin of enantioselectivity of the hetero-Claisen approach to oxindoles.

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Authors: Hongming Jin; Bin Tian; Xinlong Song; Jin Xie; Matthias Rudolph; Frank Rominger; A Stephen K Hashmi
Journal: Angew Chem Int Ed Engl Date: 2016-09-15 Impact factor: 15.336

8. Heterocycle-to-Heterocycle Route to Quinoline-4-amines: Reductive Heterocyclization of 3-(2-Nitrophenyl)isoxazoles.

Authors: Keith C Coffman; Vy Duong; Alex L Bagdasarian; James C Fettinger; Makhlouf J Haddadin; Mark J Kurth
Journal: European J Org Chem Date: 2014-12

9. Access to Structurally Diverse Quinoline-Fused Heterocycles via Rhodium(III)-Catalyzed C-C/C-N Coupling of Bifunctional Substrates.

Authors: Songjie Yu; Yunyun Li; Xukai Zhou; He Wang; Lingheng Kong; Xingwei Li
Journal: Org Lett Date: 2016-06-07 Impact factor: 6.005