One-pot synthesis of benzo[1,4]thiazin-3(4H)-ones and a Theoretical Study of the S-N type Smiles rearrangement mechanism

Yongmei Zhao; Yanmiao Wu; Jiong Jia; Dongju Zhang; Chen Ma

doi:10.1021/jo3014287

One-pot synthesis of benzo[1,4]thiazin-3(4H)-ones and a Theoretical Study of the S-N type Smiles rearrangement mechanism

J Org Chem. 2012 Oct 5;77(19):8501-6. doi: 10.1021/jo3014287. Epub 2012 Sep 14.

Authors

Yongmei Zhao¹, Yanmiao Wu, Jiong Jia, Dongju Zhang, Chen Ma

Affiliation

¹ School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China.

PMID: 22950354
DOI: 10.1021/jo3014287

Abstract

Benzo[1,4]thiazin-3(4H)-one derivatives are conveniently prepared in one pot via a Smiles rearrangement (SR) tandem reaction. In order to understand the reaction, we present here a theoretical study on the S-N type SR mechanism.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Hydrocarbons, Halogenated / chemistry*
Models, Theoretical
Molecular Structure
Thiazines / chemical synthesis
Thiazines / chemistry*

Substances

Hydrocarbons, Halogenated
Thiazines
benzo(1,4)thiazin-3(4H)-one