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
Summary
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
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