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 uncomplicated capabilities on the Ring and Their Hydrogenated Derivatives (I. Mathison & W. Solomons).

Isoquinolines Containing Oxidized Nitrogen features 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 capabilities on the Ring and Their Hydrogenated Derivatives (pages 367–477): I. W. Mathison and W. E. Solomons
Chapter IV Isoquinolines Containing Oxidized Nitrogen services and Their Hydrogenated Derivatives (pages 479–532): J. W. Bunting

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Additional resources for Chemistry of Heterocyclic Compounds: Isoquinolines, Part 2, Volume 38, Second Edition

Sample text

7 2 (Eq. 65). - b N0 O H Wc1 (65) CI 33 Ring-Halogenated Isoquinolines Treatment of the hydroxy-substitutedisoquinoline 79 and 83with phosphorus oxychloride in pyridine a t O f led to, among other products, the angular chlorinated hydrogenated isoquinolines 80 and 84'25(Eqs. 66 and 67). WN' Me WN, 81 80 79 + Me 82 C1 83 84 (ii) 8s (67) Replacement Reactions During an attempt to prepare 8-nitroisoquinoline from 5-amino-8-nitroisoquinoline (86) by deamination, Keilin and Cass observed that the product (obtained in 70% yield) was actually 8-chloroisoquinoline10' (Eq.

For example. except for the I-fluoroisomer, none of the fluoroisoquinolines have a replaceable halogen. L1S The N-oxide can also be used for the introduction of a halogen (especially chlorine or bromine) in the 1 position of the isoquinoline nucleus. 4-Bromoisoquinoline undergoes ready N-oxidation and the product (109) can easily be converted to 4-bromo- I -chloroisoquinoline by the action of phosphorus o x y c h l ~ r i d e (Eq. ’ ~ ~ 101) [see Section 11. A (c) (ii)]. c1 109 1 -Bromo- and 1 -chloroisoquinolines react with isoquinoline N-oxide to form (Eq.

86). I CrC-Me Reactions of Halogenated lsoquinolines Me0 6 MeO 0. Cl + 41 MgBr OMe OMe OMe OMe Me0 e O T k e OMe Cryptostyline I1 Sckmc 23 This method has been extended to the preparation of ethynylisoquinolines by use of 2-methyl-but-3-yn-2-01 as the protected acetylene source'66 (Scheme 24). Ethynylisoquinolines can also be prepared using trimet hylsilylacetylene and subsequent removal of the trimethylsilyl groups using aqueous methanolic 25). potassium h y d r ~ x i d e ' ~(Scheme ' Me Me I Sckmc 24 Halogenated and Metsllated lsoquinolines 48 X=I-CI.

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