One-pot synthesis of dihydroquinazolinethione-based polycyclic system

Wensheng Zhang; Xiaofeng Zhang; Xiaoming Ma; Wei Zhang

doi:10.1016/j.tetlet.2018.09.023

One-pot synthesis of dihydroquinazolinethione-based polycyclic system

Wensheng Zhang
, Xiaofeng Zhang
, Xiaoming Ma
, Wei Zhang

Chemistry

University of Massachusetts Boston
Jiaozuo Teachers’ College
Changzhou University

Research output: Contribution to journal › Article › peer-review

Abstract

A one-pot and diastereoselective synthesis of quinazoline-2(1H)-thione-containing polycyclic compounds is introduced. The reaction process includes [3 + 2] cycloaddition of azomethine ylides for pyrrolidines, Staudinger-aza-Wittig reaction of azides for iminophosphoranes, formation of isothiocyanates, and finally cyclization of amines to isothiocyanates for dihydroquinazolinethiones.

Original language	English
Pages (from-to)	3845-3847
Number of pages	3
Journal	Tetrahedron Letters
Volume	59
Issue number	43
DOIs	https://doi.org/10.1016/j.tetlet.2018.09.023
State	Published - Oct 24 2018

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Dihydroquinazolinethione
One-pot synthesis
Staudinger-aza-Wittig reactions
[3 + 2] Cycloaddition

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10.1016/j.tetlet.2018.09.023

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title = "One-pot synthesis of dihydroquinazolinethione-based polycyclic system",

abstract = "A one-pot and diastereoselective synthesis of quinazoline-2(1H)-thione-containing polycyclic compounds is introduced. The reaction process includes [3 + 2] cycloaddition of azomethine ylides for pyrrolidines, Staudinger-aza-Wittig reaction of azides for iminophosphoranes, formation of isothiocyanates, and finally cyclization of amines to isothiocyanates for dihydroquinazolinethiones.",

keywords = "Dihydroquinazolinethione, One-pot synthesis, Staudinger-aza-Wittig reactions, [3 + 2] Cycloaddition",

author = "Wensheng Zhang and Xiaofeng Zhang and Xiaoming Ma and Wei Zhang",

note = "Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd",

year = "2018",

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day = "24",

doi = "10.1016/j.tetlet.2018.09.023",

language = "English",

volume = "59",

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journal = "Tetrahedron Letters",

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T1 - One-pot synthesis of dihydroquinazolinethione-based polycyclic system

AU - Zhang, Wensheng

AU - Zhang, Xiaofeng

AU - Ma, Xiaoming

AU - Zhang, Wei

PY - 2018/10/24

Y1 - 2018/10/24

N2 - A one-pot and diastereoselective synthesis of quinazoline-2(1H)-thione-containing polycyclic compounds is introduced. The reaction process includes [3 + 2] cycloaddition of azomethine ylides for pyrrolidines, Staudinger-aza-Wittig reaction of azides for iminophosphoranes, formation of isothiocyanates, and finally cyclization of amines to isothiocyanates for dihydroquinazolinethiones.

AB - A one-pot and diastereoselective synthesis of quinazoline-2(1H)-thione-containing polycyclic compounds is introduced. The reaction process includes [3 + 2] cycloaddition of azomethine ylides for pyrrolidines, Staudinger-aza-Wittig reaction of azides for iminophosphoranes, formation of isothiocyanates, and finally cyclization of amines to isothiocyanates for dihydroquinazolinethiones.

KW - Dihydroquinazolinethione

KW - One-pot synthesis

KW - Staudinger-aza-Wittig reactions

KW - [3 + 2] Cycloaddition

UR - https://www.scopus.com/pages/publications/85053103364

UR - https://www.scopus.com/pages/publications/85053103364#tab=citedBy

U2 - 10.1016/j.tetlet.2018.09.023

DO - 10.1016/j.tetlet.2018.09.023

M3 - Article

AN - SCOPUS:85053103364

SN - 0040-4039

VL - 59

SP - 3845

EP - 3847

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 43

ER -

One-pot synthesis of dihydroquinazolinethione-based polycyclic system

Abstract

ASJC Scopus Subject Areas

Keywords

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