2,6-difunctionalization of N-substituted dithienothiazines via dilithiation

Catherine Dostert; Daniel Czajkowski; Thomas J.J. Müller

doi:10.1055/s-0033-1340307

2,6-difunctionalization of N-substituted dithienothiazines via dilithiation

Catherine Dostert, Daniel Czajkowski, Thomas J.J. Müller^*

^*Corresponding author for this work

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

12 Citations (Scopus)

Abstract

The regioselective lithiation of dithienothiazines followed by electrophilic trapping in a one-pot fashion is an efficient route to 2-mono- and 2,6-difunctionalized dithienothiazines. A pseudo five-component dilithiation-diformylation-double-Wittig olefination sequence gives a dithienothiazine symmetrically functionalized with α,β-unsaturated ester side chains in excellent yield.

Original language	English
Article number	ST-2013-B0975-L
Pages (from-to)	371-374
Number of pages	4
Journal	Synlett
Volume	25
Issue number	3
DOIs	https://doi.org/10.1055/s-0033-1340307
Publication status	Published - Feb 2014
Externally published	Yes

Keywords

Wittig reactions
addition reactions
heterocycles
lithiation
multicomponent reactions

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abstract = "The regioselective lithiation of dithienothiazines followed by electrophilic trapping in a one-pot fashion is an efficient route to 2-mono- and 2,6-difunctionalized dithienothiazines. A pseudo five-component dilithiation-diformylation-double-Wittig olefination sequence gives a dithienothiazine symmetrically functionalized with α,β-unsaturated ester side chains in excellent yield.",

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AU - Dostert, Catherine

AU - Czajkowski, Daniel

AU - Müller, Thomas J.J.

PY - 2014/2

Y1 - 2014/2

N2 - The regioselective lithiation of dithienothiazines followed by electrophilic trapping in a one-pot fashion is an efficient route to 2-mono- and 2,6-difunctionalized dithienothiazines. A pseudo five-component dilithiation-diformylation-double-Wittig olefination sequence gives a dithienothiazine symmetrically functionalized with α,β-unsaturated ester side chains in excellent yield.

AB - The regioselective lithiation of dithienothiazines followed by electrophilic trapping in a one-pot fashion is an efficient route to 2-mono- and 2,6-difunctionalized dithienothiazines. A pseudo five-component dilithiation-diformylation-double-Wittig olefination sequence gives a dithienothiazine symmetrically functionalized with α,β-unsaturated ester side chains in excellent yield.

KW - Wittig reactions

KW - addition reactions

KW - heterocycles

KW - lithiation

KW - multicomponent reactions

UR - http://www.scopus.com/inward/record.url?scp=84893814321&partnerID=8YFLogxK

U2 - 10.1055/s-0033-1340307

DO - 10.1055/s-0033-1340307

M3 - Article

AN - SCOPUS:84893814321

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JO - Synlett

JF - Synlett

IS - 3

M1 - ST-2013-B0975-L

ER -

2,6-difunctionalization of N-substituted dithienothiazines via dilithiation

Abstract

Keywords

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