Synthesis of 11,12-dihydro benzo[c]phenanthridines via a Pd-catalyzed unusual construction of isocoumarin ring/FeCl3-mediated intramolecular arene-allyl cyclization: First identification of a benzo[c]phenanthridine based PDE4 inhibitor

Thirupataiah, B.; Reddy, Gangireddy Sujeevan; Ghule, Shailendra S.; Kumar, J.S. Dileep; Mounika, Guntipally; Hossain, Kazi Amirul; Mudgal, Jayesh; Mathew, Jessy Elizabeth; Shenoy, Gautham G.; Parsa, Kishore V. L.; Pal, Manojit

doi:10.1016/j.bioorg.2020.103691

Cited by 18 publications

(2 citation statements)

References 51 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Isoquinolin-1(2 H )-ones and analogues are important nitrogen heterocycles possessing diverse bioactivities and presented in many candidates, including antitumor, anti-diabetic, anti-inflammatory and cardiovascular drugs [ 1 , 2 , 3 , 4 , 5 , 6 , 7 ] ( Figure 1 ). They are also widely used as key intermediates in variety of organic transformations to access more potent bioactive molecules [ 8 , 9 , 10 , 11 , 12 , 13 , 14 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Functionalized Isoquinolone Derivatives via Rh(III)-Catalyzed [4+2]-Annulation of Benzamides with Internal Acetylene-Containing α-CF3-α-Amino Carboxylates

et al. 2022

View full text Add to dashboard Cite

A convenient pathway to a new series of α-CF3-substituted α-amino acid derivatives bearing pharmacophore isoquinolone core in their backbone has been developed. The method is based on [4+2]-annulation of N-(pivaloyloxy) aryl amides with orthogonally protected internal acetylene-containing α-amino carboxylates under Rh(III)-catalysis. The target annulation products can be easily transformed into valuable isoquinoline derivatives via a successive aromatization/cross-coupling operation.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis of Functionalized Isoquinolone Derivatives via Rh(III)-Catalyzed [4+2]-Annulation of Benzamides with Internal Acetylene-Containing α-CF3-α-Amino Carboxylates

et al. 2022

View full text Add to dashboard Cite

show abstract

“…[4,5] Furthermore, pyridones are useful intermediates en route to densely functionalised pyridines, which are challenging to access otherwise. [6,7] The traditional methods for the synthesis of 2-pyridones include classical condensation processes of acyclic building blocks such as the Guareschi synthesis and Knoevenageltype condensations, [8,9] the reaction of 2H-pyran-2-one derivatives with ammonia, [9] the rearrangements of pyridine-N-oxides or pyridinium salts, [10,11] and transformations of the corresponding pyridine derivatives, [9] among other methods. [9,12,13] However, these pathways are often lengthy, require pre-functionalised building blocks, employ harsh conditions, or lack generality.…”

mentioning

confidence: 99%

Streamlining the Synthesis of Pyridones through Oxidative Amination

Botlik,

Weber,

Ruepp

et al. 2024

Preprint

View full text Add to dashboard Cite

Herein we report the development of an oxidative amination process for the streamlined synthesis of pyridones from cyclopentenones. Cyclopentenone building blocks can undergo in situ silyl enol ether formation, followed by the introduction of a nitrogen atom into the carbon skeleton with successive aromatisation to yield pyridones. The reaction sequence is operationally simple, rapid, and carried out in one pot. The reaction proceeds under mild conditions, exhibits broad functional group tolerance, complete regioselectivity, and is well scalable. The developed method provides facile access to the synthesis of 15N-labelled targets, industrially relevant pyridone products and their derivatives in a fast and efficient way.

show abstract

Fluorocyclization of 2‐Alkynylbenzoates: Synthesis of Fluorinated Isocoumarins by N‐Fluoropyridinium Salts

Sakagami,

Tsubouchi,

Saito

2024

Adv Synth Catal

View full text Add to dashboard Cite

Fluorocyclization of heteroatom‐centred nucleophile‐tethered unsaturated compounds is one of the most powerful methods for the synthesis of fluorinated heterocycles. However, although these reactions have often been accomplished by using transition metal catalysts along with fluorine sources, such catalytic systems have not been applicable to the reaction of 2‐alkynylbenzoates. Herein, we describe metal‐free fluorocyclization of 2‐alkynylbenzoates by N‐fluoropyridinium salts. The present method allows the selective synthesis of 4‐fluoroisocoumarins and 3,4,4‐trifluoroisochromanones by minor modification of the reaction conditions. This report provides one of the few methods for the synthesis of fluorinated isocoumarin.

show abstract

Synthesis of 11,12-dihydro benzo[c]phenanthridines via a Pd-catalyzed unusual construction of isocoumarin ring/FeCl3-mediated intramolecular arene-allyl cyclization: First identification of a benzo[c]phenanthridine based PDE4 inhibitor

Cited by 18 publications

References 51 publications

Synthesis of Functionalized Isoquinolone Derivatives via Rh(III)-Catalyzed [4+2]-Annulation of Benzamides with Internal Acetylene-Containing α-CF3-α-Amino Carboxylates

Synthesis of Functionalized Isoquinolone Derivatives via Rh(III)-Catalyzed [4+2]-Annulation of Benzamides with Internal Acetylene-Containing α-CF3-α-Amino Carboxylates

Streamlining the Synthesis of Pyridones through Oxidative Amination

Fluorocyclization of 2‐Alkynylbenzoates: Synthesis of Fluorinated Isocoumarins by N‐Fluoropyridinium Salts

Contact Info

Product

Resources

About