Chemistry of Heterocyclic Compounds: Isoquinolines, Part 2, - download pdf or read online

ISBN-10: 0470187123

ISBN-13: 9780470187128

ISBN-10: 0471628565

ISBN-13: 9780471628569

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 services 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 uncomplicated 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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Extra resources for Chemistry of Heterocyclic Compounds: Isoquinolines, Part 2, Volume 38, Second Edition

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Thus; in the presence of sodium amide, 1-chloroisoquinoline even reacts with phenylacetonitrile”. Is’ to yield compound (101) (Eq. 112). ’ s8 (Eq. 83). q N CI r-Butylthioethers can be obtained by reaction of 1-chloroisoquinoline with sodium r-butylthiolate suspension’” (Eq. 84). , 1 -Chloroisoquinoline can be alkylated or alkenylated by reaction with a Wittig reagent (alkylidene phosphorane), and hydrolysis of the resulting ylide to yield the alkyl derivative or reaction with a carbonyl compound to yield the alkenyl derivative (Scheme 21).

Attempts to overcome the disadvantages of the Bischler-Napieralsky, Pictet-Gams, and Pomeranz--Fritsch reactions which do not work well with Ring-Halogenated isoquinolines 31 electron-withdrawing substituents continue to engage the attention of chemists. Thermal electrocyclization of I-aryl-2-aza-l,3-pentadiene(91) led to the 3,4dihydroisoquinolines (92)in about 60% yield’36(Eq. 79). 13’ (Scheme 13). F F + CFJCN- F F F 93 IWcF” F F F F + 9 4 Scheme 13 F F F F t P)rol>ri\ 95 4-Bromoisoquinoline has been obtained by the acidic hydrolysis of 1,3dimethoxy-4-bromo-2-cyano- I ,2,3,4-tetrahydroisoquinoline(%), where the hydrogen atoms in positions 3 and 4 are cis oriented.

And Under Vilsmeier-Haack conditions, 3-alkoxy-5,6-dihydroisoquinolines 3-alkoxy-5,6,7,8-tetrahydroisoquinolinesare converted to the corresponding 3chlorocompounds'29 (Eqs. 69 and 70). aC Halogenated and Metallated lsoquinolines 34 - RZ @OM' R2 Rl R' R ' = Me, R Z = CN -w R ' = Ph-CH2, RZ = CN R ' = Me, R2 = H RZ Qx R' R' X=OMe, OH, OCH,Ph R' =Me, CH,Ph, H R2=CN, H 3Br (iii) Cleavage Reactions The base-catalyzed cleavage of bisisoquinoline (87) has been reported to lead (Eq. 71). to a I-bromoisoq~inoline'~~ N-COCHj __c 0N-COCHj \ Br (71) 87 (iv) Interconversions Replacement of one halogen by another has also been used for the synthesis of certain difficult to obtain isoquinoline derivatives.

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


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