Heterocyclic Chemistry at a Glance
Quinolines and Isoquinolines 65 ‘Reissert compounds’ are formed when quinoline or isoquinoline is reacted with an acid chloride, ...
66 Quinolines and Isoquinolines Oxidation and reduction N-Alkylquinolinium and -isoquinolinium salts are oxidised in alkaline s ...
Quinolines and Isoquinolines 67 Oxygen substituents Quinolines and isoquinolines with hydroxyl groups on the benzene rings are n ...
68 Quinolines and Isoquinolines In a very similar approach, an ,-unsaturated ketone or aldehyde can be employed, though, as th ...
Quinolines and Isoquinolines 69 Synthesis of isoquinolines from 2-arylethamines (1,2- and 1,8a-bonds made) The trivial conversio ...
70 Quinolines and Isoquinolines Synthesis of isoquinolines from ortho-alkynyl aryl-aldehydes or corresponding imines (2,3-bond m ...
Heterocyclic Chemistry at a Glance, Second Edition. John A. Joule and Keith Mills. © 2013 John Wiley & Sons, Ltd. Published ...
72 Pyryliums, Benzopyryliums, Pyrones and Benzopyrones The reaction of pyrylium salts with ammonia (or primary amines) produces ...
Pyryliums, Benzopyryliums, Pyrones and Benzopyrones 73 Oxygen substituents – pyrones and benzopyrones The deprotonation of a hyd ...
74 Pyryliums, Benzopyryliums, Pyrones and Benzopyrones ammonia or amines – clearly, in these transformations the ammonia/amine m ...
Pyryliums, Benzopyryliums, Pyrones and Benzopyrones 75 that abstracts hydride from the intermediate 4H-pyran is the triphenylmet ...
76 Pyryliums, Benzopyryliums, Pyrones and Benzopyrones produces 2-pyrone and bromination gives 3,5-dibromo-2-pyrone. (Note the e ...
Pyryliums, Benzopyryliums, Pyrones and Benzopyrones 77 Exercises Devise a mechanism to explain the formation of 1,3,5-triphenyl ...
Heterocyclic Chemistry at a Glance, Second Edition. John A. Joule and Keith Mills. © 2013 John Wiley & Sons, Ltd. Published ...
Pyrroles 79 -position. An N-trialkylsilyl substituent can be subsequently easily removed using fl uoride, to provide an N-hydro ...
80 Pyrroles N-Deprotonation and N-metallated pyrroles TheN-hydrogen of pyrrole can be quantitatively removed with strong bases g ...
Pyrroles 81 Pyrrolyllithiums can also be generated via metal-halogen exchange processes. Palladium(0)-catalysed reactions Pyrrol ...
82 Pyrroles Pericyclic reactions Pyrroles, as aromatic molecules, do not generally behave as dienes. However, when an electron-w ...
Pyrroles 83 Ring synthesis – disconnections There are three important disconnections for the construction of pyrroles, summarise ...
84 Pyrroles nucleophilic addition to generate the N-1-C-2 bond are involved, though the exact order of events is not certain – p ...
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