1,2-Dihydroisoquinolines—XXI

Dyke, S.F.; Thorns, J.F.; Hedges, Stuart H.; Wiggins, D. W.

doi:10.1016/0040-4020(79)80011-3

Cited by 7 publications

(1 citation statement)

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“…При нагріванні ізокумарину у спиртовому розчині MeNH2 у відкритому посуді слід мати на увазі, що концентрація леткого аміну швидко падає. Авторами методики [33] ця проблема була розв'язана шляхом періодичного додавання аміну (рис. 19).…”

Section: рис 18 трансформація 3-арилізокумарину у 3-арил-n-метилізоunclassified

Using of 3-Arylisocoumarins in 3-Arylisoquinolons Synthesis

Shablykina

Москвина

Савченко

et al. 2017

Bull. T. Shevchenko Nat. Univ. Kyiv. Chem.

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The review systematizes and analyzes the literature data (100 sources) regarding the recyclization of 3-arylisocoumarins (3-aryl-1H-isochromen-1-ones) under the action of primary N-nucleophiles that leads to the formation of 3-arylisoquinolones (3-arylisoquinolin-1(2H)-ones). This reaction may be carried out with a wide range of primary aminogroup-containing compounds: ammonia, primary aliphatic, aromatic, and heteroaromatic amines, hydrazine, and hydroxylamine. This transformation is not hindered by the presence of active functional groups (hydroxyl, acetal, carboxyl, ester, nitrile groups, or additional aminogroup) neither in 3-arylcoumarin nor in the primary amine. A special attention has been paid to reaction conditions (temperature regime, duration, solvent, catalysts), which may vary greatly. In particular, it is pointed out that in most cases to carry out high-temperature recyclization of 3-arylisocoumarins with ammonia and volatile amines with low molecular weight the use of closed reactors and high-pressure flasks was required. The cases of successful recyclization of 11,12-dihydrodibenzo[c,h]chromen-6-ones, indeno[1,2-c]isochromen-5(11H)-ones, isochromeno[4,3-c]chromen-6,11-dione and 5H-benzofuro[3,2-c]isochromen-5-one are reviewed separately. The polycondensated heterocyclic system of these compounds contains a 3-arylisocoumarin fragment. The biological activity data is presented for the compounds obtained via this transformation – 3-arylisoquinolin-1(2H)-ones, and also polycondensated systems that contain this fragment, e.g. 11,12-dihydrobenzo[c]phenanthridin-6(5H)-ones and 6H-indeno[1,2-c]isoquinoline-5,11-diones. The opportunities to use 3-arylisoquinolin-1(2H)-ones in the synthesis of other compounds of isoquinoline family, e.g. natural benzo[c]phenanthridinealocoloids, are demonstrated.

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Section: рис 18 трансформація 3-арилізокумарину у 3-арил-n-метилізоunclassified

Using of 3-Arylisocoumarins in 3-Arylisoquinolons Synthesis

Shablykina

Москвина

Савченко

et al. 2017

Bull. T. Shevchenko Nat. Univ. Kyiv. Chem.

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The Vilsmeier Reaction of Non‐Aromatic Compounds

Jones

Stanforth

2000

Organic Reactions

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This chapter extends the discussion to reactions between the Vilsmeier‐Haack reagent (subsequently referred to as the Vilsmeier reagent for brevity) and any other compounds in which a carbon‐carbon bond is formed. The discussion thus excludes reactions in which the Vilsmeier reagent acts as a chlorinating agent (for example in the preparation of acid chlorides), or in which it forms carbon‐oxygen or carbon‐nitrogen bonds, unless these are accompanied by formation of a carbon‐carbon bond. For a discussion of the nature of the reagent and of the mechanism of the reaction, the earlier chapter in vol. 49 should be consulted. There are also a number of reviews that deal at length with mechanisms of reactions involving the Vilsmeier reagent, notably those by Jutz and Marson, and hence this chapter will concentrate on applications, with brief mention of mechanisms when necessary. Wizinger has pointed out that alkenes could react with the Vilsmeier reagent, but his only examples were styrenes where the intermediate carbocation has considerable stability. Hydrolysis gives the cinnamaldehyde. In principle, any alkene which is not too sterically hindered can undergo this reaction, but the Vilsmeier reagent has low reactivity as an electrophile, and in practice activation is often necessary. The addition depends on the HOMO of the alkene, and anything increasing the HOMO energy will aid reaction, as for example further conjugation (dienes, trienes, etc.) or the presence of an electron‐donating substituent. Hence aldehydes and ketones are active in their enol forms, and enol ethers and enamines are good substrates. Indeed, all additions covered by this chapter can be regarded as alkene additions, even those on active methyl groups attached to electron‐deficient rings. As with any reaction involving carbocation intermediates, rearrangements are possible; the initial products are sometimes enamines, and this can give rise to polysubstitution. The substrates are grouped into eleven major subsections; references to reviews of particular relevance will be found in the appropriate subsection.

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