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Synthesis 2018; 50(06): 1209-1227
DOI: 10.1055/s-0037-1609175
short review
© Georg Thieme Verlag Stuttgart · New York

Cyclization Reactions for the Synthesis of Phthalans and Isoindolines­

Gianluigi Albano 
Department of Chemistry and Industrial Chemistry, University of Pisa, Via G. Moruzzi 13, 56124 Pisa, Italy   Email: Laura.Antonella.Aronica@unipi.it
,
Laura Antonella Aronica  *
Department of Chemistry and Industrial Chemistry, University of Pisa, Via G. Moruzzi 13, 56124 Pisa, Italy   Email: Laura.Antonella.Aronica@unipi.it
› Author AffiliationsUniversity of Pisa (PRA_2017_28) is gratefully acknowledged for funding.
Further Information

Publication History

Received: 27 November 2017

Accepted after revision: 18 December 2017

Publication Date:
31 January 2018 (online)

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Abstract

Oxygen and nitrogen heterocycles are present in a vast number of natural substrates and biologically active molecules. In particular, phthalan and isoindoline subunits are found in many classes of products such as antibiotics, antioxidants, antimycotics, pigments, and fluorophores. Therefore several procedures dedicated to the construction of these heterocycles have been developed. In this review, a detailed analysis of the literature data regarding the synthesis of these nuclei via cyclization reactions is reported.

1 Introduction

2 Phthalans

2.1 Oxa-Pictet–Spengler Reaction

2.2 Garratt–Braverman Cyclization

2.3 Diels–Alder and Related Reactions

2.4 [2+2+2] Cyclotrimerization of Alkynes

2.5 Cycloetherification of ortho-Substituted Aromatics

2.6 Tandem Carbonylative Sonogashira Coupling–Cyclization Reactions

3 Isoindolines

3.1 Amination of Dihalides

3.2 Intramolecular Hydroamination

3.3 Diels–Alder and Related Reactions

3.4 [2+2+2] Cycloaddition Reactions

3.5 Tandem Carbonylative Sonogashira Coupling–Cyclization Reactions

4 Conclusions

Key words

phthalan - isoindoline - cyclization - transition-metal catalysis - Sonogashira reaction