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

14 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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title = "2,6-difunctionalization of N-substituted dithienothiazines via dilithiation",

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.",

keywords = "Wittig reactions, addition reactions, heterocycles, lithiation, multicomponent reactions",

author = "Catherine Dostert and Daniel Czajkowski and M{\"u}ller, \{Thomas J.J.\}",

year = "2014",

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doi = "10.1055/s-0033-1340307",

language = "English",

volume = "25",

pages = "371--374",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

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T1 - 2,6-difunctionalization of N-substituted dithienothiazines via dilithiation

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 - https://www.scopus.com/pages/publications/84893814321

U2 - 10.1055/s-0033-1340307

DO - 10.1055/s-0033-1340307

M3 - Article

AN - SCOPUS:84893814321

SN - 0936-5214

VL - 25

SP - 371

EP - 374

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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