Download Chemistry of Heterocyclic Compounds: Isoquinolines, Part 2, PDF

Halogenated and Metallated Isoquinolines and Their Hydrogenated Derivatives (M. Nair & M. Premila).

Isoquinoline Carboxylic Acids and Their Hydrogenated Derivatives (F. Popp & F. Duarte).

Isoquinolines Containing easy features on the Ring and Their Hydrogenated Derivatives (I. Mathison & W. Solomons).

Isoquinolines Containing Oxidized Nitrogen capabilities and Their Hydrogenated Derivatives (J. Bunting).

IndexContent:
Chapter I Halogenated and Metallated Isoquinolines and Their Hydrogenated Derivatives (pages 1–133): M. D. Nair and M. S. Premila
Chapter II Isoquinoline Carboxylic Acids and Their Hydrogenated Derivatives (pages 135–365): F. D. Popp and F. F. Duarte
Chapter III Isoquinolines Containing simple services on the Ring and Their Hydrogenated Derivatives (pages 367–477): I. W. Mathison and W. E. Solomons
Chapter IV Isoquinolines Containing Oxidized Nitrogen capabilities and Their Hydrogenated Derivatives (pages 479–532): J. W. Bunting

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Extra info for Chemistry of Heterocyclic Compounds: Isoquinolines, Part 2, Volume 38, Second Edition

Example text

61). Me 73 aR,=CI bR,=H cR,=H R, 74 Rz=H Rz=H Rz=CI R2 R3=H R3=CI R,=CI R3 75 Such observations have precedence in Friedel-Crafts literature and are rationalized by an isomerization of the initially formed carbonium ion 76 to the more stable 2" carbonium ion 77. Thus. in 73a-c, attack by the carbonium ion on the deactivated ring is slow relative to isomerization to 77, resulting in predominant formation of 74a-c (Scheme 12). + R1y$ NH R2 R1@" R2 R' R' 76 1 74 75a 1 77 0-c (h) Miscellaneous Methods (i!

Isoquinolines Substituted by Different Halogens Mixed haloisoquinolines have been prepared by various methods. For example, 1 -bromo-3-fluoroisoquinoline is obtained by a Schiemann reaction on 3-amino-l-bromoisoquinoline,' while 4-bromo- 1 -chloroisoquinoline is conveniently prepared by the Meisenheimer rearrangement of 4-bromoisoquinoline N - ~ x i d e In . ~ general, ~ 1 -chloroisoquinoline carrying other substituents, halogens or otherwise, are preferably synthesized from the N-oxides. '' 111.

Fluoroisoquinolines The relatively few Ruoroisoquinolines reported in the literature have been synthesized by the Schiemann reaction, starting with the appropriate amino compounds. 2' Lithium aluminium hydride reduction selectively removes the I-fluorine, yielding hexafluoroisoquinoline. E. lodoisoquinolines Not many iodoisoquinolines are reported in the literature. The Sandmeyer reaction"- ' I - ) and the replacement of chlorine by iodineI3' are the methods of choice for the synthesis of iodoisoquinolines.

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