| 词条 | Barton–Zard reaction |
| 释义 |
The Barton–Zard reaction is a route to pyrrole derivatives via the reaction of a nitroalkene with an α-isocyanoacetate under basic conditions.[1] It is named after Derek Barton and Samir Zard who first reported it in 1985.[2] MechanismThe mechanism consists of five steps:
ScopeThe nitro compound may be aromatic rather than just an alkene.[3] The reaction has been used for the synthesis of polypyrroles, including porphyrins,[4] as well as dipyrromethenes such as BODIPY.[5] References1. ^{{cite book | author =Jie Jack Li | title =Heterocyclic Chemistry in Drug Discovery | publisher =Wiley | location =New York | year =2013 | isbn =9781118354421| url =https://books.google.com/books?id=p_fM6CuK6xcC}} pp.43-4 {{DEFAULTSORT:Barton-Zard synthesis}}2. ^{{cite journal|last1=Barton|first1=Derek H. R.|last2=Zard|first2=Samir Z.|title=A new synthesis of pyrroles from nitroalkenes|journal=Journal of the Chemical Society, Chemical Communications|date=1985|issue=16|pages=1098|doi=10.1039/C39850001098}} 3. ^{{cite journal|last1=Lash|first1=Timothy D.|last2=Novak|first2=Bennett H.|last3=Lin|first3=Yanning|title=Synthesis of phenanthropyrroles and phenanthrolinopyrroles from isocyanoacetates: An extension of the barton-zard pyrrole condensation|journal=Tetrahedron Letters|date=April 1994|volume=35|issue=16|pages=2493–2494|doi=10.1016/S0040-4039(00)77152-8}} 4. ^{{cite journal|last1=Finikova|first1=Olga S.|last2=Cheprakov|first2=Andrei V.|last3=Beletskaya|first3=Irina P.|last4=Carroll|first4=Patrick J.|last5=Vinogradov|first5=Sergei A.|title=Novel Versatile Synthesis of Substituted Tetrabenzoporphyrins|journal=The Journal of Organic Chemistry|date=January 2004|volume=69|issue=2|pages=522–535|doi=10.1021/jo0350054|pmid=14725469}} 5. ^{{cite journal|last1=Ono|first1=Noboru|title=Barton-Zard Pyrrole Synthesis and Its Application to Synthesis of Porphyrins, Polypyrroles, and Dipyrromethene Dyes|journal=HETEROCYCLES|date=2008|volume=75|issue=2|pages=243|doi=10.3987/REV-07-622}} 2 : Heterocycle forming reactions|Name reactions |
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