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 capabilities on the Ring and Their Hydrogenated Derivatives (I. Mathison & W. Solomons).
Isoquinolines Containing Oxidized Nitrogen features and Their Hydrogenated Derivatives (J. Bunting).
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 easy features 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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Extra resources for Chemistry of Heterocyclic Compounds: Isoquinolines, Part 2, Volume 38, Second Edition
Treatment of benzylic halides and mesylates with the sodium anion of N-tosyl aminoacetaldehyde dimethylacetal (54) led to 55, cyclization of which led to the isoquinoline S i 9 1 (Scheme 10). 26 Halogenated and Metallated lsoquinolines OMe OMe OMe Me0 Br NaNTs X OMe Me0 - Br 54 55 TS= Tos~I X = Br, OMS OMe Me0 Br (iii). One-Step Perchloroisoquinoline Synthesis c’w An intramolecular chlorination-cyclization reaction has been reported”’ to yield perchloroisoquinoline (57) in 25% yield (Eq. 47). CI CHZCHJ CI:KCl* urn CN (47) CI CI CI 57 (f) Sundmeyer und Schiemunn Reuctions (i) Sandmeyer Reaction In many ways, the Sandmeyer and Schiemann reactions constitute the most general synthetic methods for the synthesis of haloisoquinolines.
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.
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! Rearrangements Rearrangements leading directly to haloisoquinolines have not been of much preparative value in isoquinoline chemistry. The cyclic hydroxamic acid Nhydroxyisocarbostyril (78) reacts with phosphorus oxychloride to yield I ,4- 32 Halogenated and Metallated lsoquinolines dichloroisoquinolineSY(Eq.
Chemistry of Heterocyclic Compounds: Isoquinolines, Part 2, Volume 38, Second Edition