Abstract

This review covers recent advances in synthesis of azocine-containing systems. The most approaches towards azocines are discussed.1 Introduction2 Ring-Expansion Reaction2.1 Ring-Expansion Reaction of Cyclopentane Containing the 1,4-Diketone Moiety with Primary Amines (from 5 to 8)2.2 Ring-Expansion Reaction of Annulated Tetrahydropyridines under the Action of Activated Alkynes (from 6 to 8)2.3 Reductive Ring-Expansion Reaction of Cyclic Oximes2.4 Other Ring-Expansion Reactions3 Heck Reaction4 Cycloaddition5 Ring-Closing Metathesis (RCM)6 Cyclization6.1 Metal-Catalyzed Cyclization6.2 Radical Cyclization6.3 Friedel–Crafts Cyclization6.4 Other Examples of Cyclizations7 Microwave- and Photo-Assisted Reactions8 Other Methods8.1 Cascade and Tandem Reactions8.2 Aldol Condensation8.3 Thermolysis8.4 Ring Opening8.5 Other Methods9 Conclusion

Highlights

  • 2 Ring-Expansion Reaction 2.1 Ring-Expansion Reaction of Cyclopentane Containing the 1,4-Diketone Moiety with Primary Amines 2.2 Ring-Expansion Reaction of Annulated Tetrahydropyridines under the Action of Activated Alkynes 2.3 Reductive Ring-Expansion Reaction of Cyclic Oximes 2.4 Other Ring-Expansion Reactions 3 Heck Reaction 4 Cycloaddition 5 Ring-Closing Metathesis (RCM) 6 Cyclization 6.1 Metal-Catalyzed Cyclization 6.2 Radical Cyclization 6.3 Friedel–Crafts Cyclization 6.4 Other Examples of Cyclizations 7 Microwave- and Photo-Assisted Reactions 8 Other Methods 8.1 Cascade and Tandem Reactions 8.2 Aldol Condensation 8.3 Thermolysis 8.4 Ring Opening 8.5 Other Methods

  • The chemistry of annulated azocines has not been explored in detail owing to the lack of efficient methods for their synthesis

  • This review highlights most recent approaches towards annulated azocine derivatives published after the year 2009; the previous review was published in 2008.1

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Summary

Introduction

The chemistry of annulated azocines has not been explored in detail owing to the lack of efficient methods for their synthesis. The only exception is azocinoindoles, which have been investigated extensively due to the great number of alkaloids with an azocinoindole fragment in their structure. This review highlights most recent approaches towards annulated azocine derivatives published after the year 2009; the previous review was published in 2008.1. Me N Ph (a) SOCl2, MeOH, 0–85 °C, 24 h; (b) CH2=CHCO2tBu, Pd(OAc)[2], PPh3, Et3N, DMF, 110 °C, 18 h; (c) Pd/C (cat.), H2 (1 atm), iPrOH, 23 °C, 22 h; (d) NaH, THF, 0–50 °C, 1 h; (e) PhCOCH2Br, K2CO3, acetone, 40 °C, 2 h; (f) MeNH2, THF, 100 °C, 16 h

Ring-Expansion Reactions
Reductive Ring-Expansion Reaction of Cyclic Oximes
Other Ring-Expansion Reactions
Heck Reaction
Ph O RN
Cycloaddition
Metal-Catalyzed Cyclization
Radical Cyclization
Friedel–Crafts Cyclization
Other Examples of Cyclization
H S NS H 276
Microwave- and Photo-Assisted Reactions
Cascade and Tandem Reactions
Aldol Condensation
Thermolysis
Ring Opening
Other Methods
Conclusion
Findings
Funding Information

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