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Solid-Phase Synthesis of Seven-Membered Heterocycles with Two Nitrogen Atoms

  • Veronika Fülöpová
  • Miroslav SouralEmail author
Chapter
Part of the Topics in Heterocyclic Chemistry book series (TOPICS, volume 52)

Abstract

Due to the importance of diazepines and diazepanes in medicinal chemistry and chemical biology, their preparation from diverse starting materials has been frequently reported. In this chapter, we summarize all strategies employing the method of solid-phase synthesis. More than seventeen different types of target compounds are accessible. The individual approaches are grouped according to the type of the target scaffold.

Keywords

Benzodiazepines Combinatorial chemistry Diazepanes Diazepines Solid-phase synthesis 

Abbreviations

AA

Amino acid

Boc

t-Butyloxycarbonyl

BAL

Backbone amide linker

BTC

Bis(trichloromethyl) carbonate

DABCO

1,4-Diazabicyclo[2.2.2]octane

DBU

1,8-Diazabicyclo[5.4.0]undec-7-ene

DCC

N,N′-Dicyclohexylcarbodiimide

DCE

Dichloroethane

DCM

Dichloromethane

DIAD

Diisopropyl azodicarboxylate

DIBAL-H

Diisobutylaluminium hydride

DIC

N,N′-Diisopropylcarbodiimide

DIEA

N,N-Diisopropylethylamine

DEAD

Diethyl azodicarboxylate

DECP

Diethyl cyanophosphonate

DMAP

4-Dimethylaminopyridine

DMF

N,N-Dimethylformamide

DMSO

Dimethyl sulfoxide

DMTMM

4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride

EEDQ

N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline

Fmoc

Fluorenylmethoxycarbonyl

HATU

[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate)

HOBt

1-Hydroxybenzotriazole

MBHA

Methylbenzhydrylamine

NMP

N-Methylpyrrolidone

Nos

Nitrobenzenesulfonyl

TBTU

N,N,N′,N′-Tetramethyl-O-(benzotriazol-1-yl)uronium tetrafluoroborate

TBP

Tributylphosphine

TEA

Triethylamine

THF

Tetrahydrofuran

TFA

Trifluoroacetic acid

TFMSA

Trifluoromethanesulfonic acid

TPP

Triphenylphosphine

Notes

Acknowledgments

The authors are grateful to project CZ.1.07/2.3.00/20.0009 from the European Social Fund and the National Program of Sustainability (project LO1304).

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© Springer International Publishing AG 2017

Authors and Affiliations

  1. 1.Department of Organic Chemistry, Institute of Molecular and Translational Medicine, Faculty of SciencePalacky UniversityOlomoucCzech Republic

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