Literature DB >> 21384885

Intramolecular cyclization of in situ generated adducts formed between thioamide dianions and thioformamides leading to generation of 5-amino-2-thiazolines and 5-aminothiazoles, and their fluorescence properties.

Toshiaki Murai1, Fumihiko Hori, Toshifumi Maruyama.   

Abstract

Reactions of thioamide dianions, derived from secondary N-arylmethyl thioamides using BuLi, with thioformamides followed by the addition of iodine to yield 5-amino-2-thiazolines are described. Treatment of the 5-amino-2-thiazolines with iodine leads to a highly efficient production of 5-aminothiazoles. When N,N-diarylthioformamides are employed in this process, fluorescent 5-N,N-diarylthiazoles are obtained.

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Year:  2011        PMID: 21384885     DOI: 10.1021/ol200231z

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  2 in total

1.  Acid-Responsive Absorption and Emission of 5-N-Arylaminothiazoles: Emission of White Light from a Single Fluorescent Dye and a Lewis Acid.

Authors:  Kirara Yamaguchi; Toshiaki Murai; Jing-Dong Guo; Takahiro Sasamori; Norihiro Tokitoh
Journal:  ChemistryOpen       Date:  2016-08-02       Impact factor: 2.911

2.  Dimethylamine as the key intermediate generated in situ from dimethylformamide (DMF) for the synthesis of thioamides.

Authors:  Weibing Liu; Cui Chen; Hailing Liu
Journal:  Beilstein J Org Chem       Date:  2015-09-23       Impact factor: 2.883

  2 in total

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