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Quinazoline Alkaloids and Related Chemistry

  • Shoji EguchiEmail author
Chapter
Part of the Topics in Heterocyclic Chemistry book series (TOPICS, volume 6)

Abstract

Recent progress in quinazoline alkaloids and related chemistry was reviewed focusing on developments of the synthetic methodologies and their synthetic applications. A brief historical background, aza–Wittig methodology, microwave-assisted synthesis, solid-phase synthesis, and a variety of new syntheses of quinazoline compounds by organometallic reagents, metal-catalyzed reactions, heterocyclizations, pericyclic reactions, etc. are briefly reviewed. Selected topics of total synthesis of various types of quinazoline alkaloids including substituted type like febrifugine and heterocycle-fused type such as pyrroloquinazolines, indolopyridoquinazolines, pyrazinoquinazolines, and pyrroloquinazolinoquinolines, etc. by these methodologies are discussed.

Aza–Wittig reaction Quinazolinone annelation Quinazoline alkaloids Microwave-assisted synthesis Solid-phase synthesis 

Abbreviations

aq

Aqueous

BOP

Benzotriazol-1-yloxytris(dimethylamino)phosphoniumhexafluorophosphate (peptide coupling agent)

i-Bu

Iso-butyl

CCK

Cholecystokinin

Cy3P

Tricyclohexylphosphine

1,2-DCE

1,2-Dichloroethane

DCI

1,3-Diisopropylcarbodiimide

DCM

Dichloromethane

Dppp

Bis(diphenylphosphino)propane

DS

Dodecyl sulfate

MCRs

Multi-component reactions

MDR

Multi-drug resistance

μw(MW)

Microwave

refl

Reflux

SAR

Structure activity relationship

TBP

Tributylphosphine

TPP

Triphenylphosphine

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Notes

Acknowledgments

The author express his sincere gratitude to the dedicated, hardworking, skillful efforts of his coworkers whose names appear in references cited. The author would like to express his appreciation to the Ministry of Education, Science, Sports and Culture, Japan for the generous support by Grants-in-Aid for Scientific Research.

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Authors and Affiliations

  1. 1.Department of Molecular Design and Engineering, Graduate School of EngineeringNagoya UniversityNagoyaJapan

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