Synthesis of isoquinolines through the coupling of Fischer carbene complexes with o-alkynylpyridine carbonyl derivatives

Mukherjee, Somenath; Jana, Gouranga P.; Ghorai, Binay K.

doi:10.1016/j.jorganchem.2009.08.019

Cited by 12 publications

(5 citation statements)

References 54 publications

(49 reference statements)

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“…When an olefinic tether was present, intramolecular Diels-Alder cycloaddition occurred followed by ring opening to yield tricyclic alcohols [251].…”

Section: Scheme 62mentioning

confidence: 99%

The chemistry of group-VIb metal carbonyls

Kaushik¹,

Singh²,

Kumar³

2012

Eur. J. Chem.

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KEYWORDSThe special interest attached to the chemistry of metal carbonyls arises from several causes. While quite distinct from the metal carbonyls in the organometallic compounds, they differ in physical properties (e.g., their volatility) from all other compounds of the transition metals. Chemically, they constitute a group of compounds in which the formal valency of the metal atoms is zero, and in this respect (apart, perhaps, from the ammoniates of the alkali metals) they are comparable only with the recently discovered compounds. As a class, the carbonyls are reactive compounds, and a number of new types of inorganic compounds have been discovered. In the concepts for new products, performance, product safety, and product economy criteria are equally important. They are taken into account already when the raw material base for a new industrial product development is defined. Since the discovery of nickel carbonyl by Mond and Langer in 1888, the carbonyls of the iron group and of chromium, molybdenum and tungsten have found important technical applications, e.g., in the Mond nickel process, and for the preparation of the metals in a state of subdivision and of purity suitable for powder metallurgy, for catalysts, etc. The reaction mechanism of the processes developed for producing the carbonyls technically has only recently received its interpretations. Within the space of review it is necessary to limit discussion to a few topics. Particular stress has accordingly laid upon (a) the chemical bonding in metal carbonyls, (b) importance of IR and NMR spectroscopy in characterization of metal carbonyls, (c) substitution reactions of G-VIb metal carbonyls, (d) kinetics and mechanism of substitution reactions in metal carbonyls, (e) substituted complexes of G-VIb metal carbonyl, (f) chelate complexes of G-VIb metal carbonyls, (g) uses of G-VIb metal carbonyl complexes and (h) studies done on G-VIb metal carbonyls.

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“…When an olefinic tether was present, intramolecular Diels-Alder cycloaddition occurred followed by ring opening to yield tricyclic alcohols [251].…”

Section: Scheme 62mentioning

confidence: 99%

The chemistry of group-VIb metal carbonyls

Kaushik¹,

Singh²,

Kumar³

2012

Eur. J. Chem.

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“…42 Under the reaction conditions, the sequence does not stop at adducts XLII. Similar tandem approaches, but using alkynyl heteroaromatic carbonyl compounds 114 (X = O), have led to the syntheses of compounds of types 117 and 118, such as nitrogen-containing heterocyclic analogues of 1-arylnaphthalene lignans, 43 phenanthridine ring systems 44 or isoquinoline derivatives 45 (Scheme 30). Two major strategies have been developed to carry out intramolecular versions of these reaction sequences.…”

Section: Domino Reactions 61 Isobenzofuran Cyclization/diels-alder Cmentioning

confidence: 99%

“…In one of them, the dienophile is linked to the carbene partner, as in 119. Alkenes have been used as dienophiles in most of the cases, [43][44][45][46] leading to polycyclic structures such as 120 in reactions involving alkynyl carbonyl compounds 114 (X = O). Occasionally, enol ether hydrolysis, aromatization of the newly formed ring or carbonyl insertion in the oxygen bridge may take place leading to adducts such as 121, 122 or 123.…”

Section: Domino Reactions 61 Isobenzofuran Cyclization/diels-alder Cmentioning

confidence: 99%

Multi-component reactions involving group 6 Fischer carbene complexes: a source of inspiration for future catalytic transformations

2010

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The ability of heteroatom stabilized Fischer carbene complexes (FCCs) to participate in multicomponent reactions (MCRs) has become a characteristic of such organometallics, particularly of chromium carbenes. This feature article updates the main results in this field during the last lustrum, highlighting the ability of FCCs for the construction of densely functionalized frameworks, mainly through the successive incorporation of unsaturated moieties (alkynes, CO ligands,. . .) in a sequential manner. Examples where up to seven components are coupled will be presented.

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“…Additionally, 2-alkynylpyridines represent synthetically relevant intermediates in organic synthesis, because their triple bonds could readily undergo diverse transformations, such as annulation [3], cyclization [4], or 1,3-dipolar cycloaddition [5]. In this context, these compounds contribute to the construction of a large array of heterocyclic frameworks, including azaindoles [6,7], furo [3,4-b]pyridines [8], indolizines [9], isoquinolines [10], aryl-substituted pyridines [11], and N-metallacycles [12]. As a result, the construction of functionalized 2-alkynylpyridines constitutes an attractive challenge, considering the synthetic and biological aspects of this scaffold.…”

Section: Introductionmentioning

confidence: 99%

Unexpected formation of 2-alkynylpyridines from iodo-selenopyridines by selective activation of C Se over C I bonds

Tran

Lefèvre

Haddad

et al. 2019

Catalysis Communications

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Synthesis of isoquinolines through the coupling of Fischer carbene complexes with o-alkynylpyridine carbonyl derivatives

Cited by 12 publications

References 54 publications

The chemistry of group-VIb metal carbonyls

The chemistry of group-VIb metal carbonyls

Multi-component reactions involving group 6 Fischer carbene complexes: a source of inspiration for future catalytic transformations

Unexpected formation of 2-alkynylpyridines from iodo-selenopyridines by selective activation of C Se over C I bonds

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