2-Benzyliden-2H-thieto[3,2-b]quinoline: a new heterocycle and its rearrangement to 2-phenylthieno[3,2-b]quinoline

Haddadin, Makhluf J.; El-Nachef, Claudia; Kisserwani, Hawraa; Chaaban, Yara; Kurth, Mark J.; Fettinger, James C.

doi:10.1016/j.tetlet.2010.10.039

Cited by 9 publications

(3 citation statements)

References 14 publications

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“…Suen et al [ 14 ] reported the synthesis of the thietanone 36 through the reaction of 4‐phenylbutan‐2‐one 35 with thionyl chloride in pyridine, Friedländer reaction between 2‐aminobenzaldehydes 31 and thietanone 36 in 10% KOH in ethanol at room temperature gave the desired (Z)‐2‐phenyliden‐2H‐thieto [3, 2‐ b ]quinolines 37a‐c . Whereas repeating the same reaction under reflux temperature achieved the 2‐phenylthieno[3,2‐ b ]quinolines 38a‐c , [ 15 ] (Scheme 5).…”

Section: Synthesis and Reactivitymentioning

confidence: 99%

Recent progress on the chemistry of thieno[3,2‐b]quinoline derivatives (part III)

Gouda

Abu‐Hashem

Abdelgawad

2020

Journal of Heterocyclic Chem

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Section: Synthesis and Reactivitymentioning

confidence: 99%

Recent progress on the chemistry of thieno[3,2‐b]quinoline derivatives (part III)

Gouda

Abu‐Hashem

Abdelgawad

2020

Journal of Heterocyclic Chem

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“…recently found that the Friedländer reaction of 2‐aminoaryl aldehydes and ketones with β‐ketoesters could even be performed in the absence of exogenous catalyst . When 2‐aminobenzaldehyde was used, the 1,3‐dicarbonyl component in the Friedländer reaction could be replaced by many other counter‐reagents, such as diketene, β‐functionalized ketones, cyanoacetamides, 2‐amino‐1‐methyl‐2‐imidazolin‐5‐one, and thietanone derivatives . Li et al.…”

Section: Benzaldo‐x Bifunctional Building Blocks and Their Heterocyclmentioning

confidence: 99%

Aldo‐X Bifunctional Building Blocks for the Synthesis of Heterocycles

Ravichandiran

Lai

2016

The Chemical Record

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Compounds containing oxygen, nitrogen, or sulfur atoms inside the rings are attracting much attention and interest due to their biological importance. In recent years, several methods for the synthesis of such molecules have been reported by using aldo-X bifunctional building blocks (AXB3 s) as substrates; these are a wide class of organic molecules that contain at least two reactive sites, among them, one aldehyde, acetal, or semiacetal group was involved. Because of the multiple reactivities, AXB3 s are widely used in the one-pot synthesis of biologically important heterocycles. This review summarizes the synthesis of important heterocycles by using AXB3 s as pivotal components in establishing multicomponent reactions, tandem reactions, and so forth. In many cases, the established reaction systems with AXB3 s were characterized by some green properties, such as easy access to the substrate, mild and environmentally benign conditions, and wide scope of the substrate.

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“…Due to their significance, numerous synthetic approaches have been developed for the construction of such structural motifs. These approaches could be categorized simply into three strategies on the basis of the ring-constructing method ( Figure 1 ), which are the heteroaryl ring formation (strategy a) [ 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 ], the central pyridyl ring formation (strategy b) [ 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 ], and the formation of both rings (strategy c) [ 4 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 ]. Although there are advantages and disadvantages to each strategy from various aspects, the strategy b seems to be the most user-friendly in terms of the accessibility of the starting substrates.…”

Section: Introductionmentioning

confidence: 99%

Indium-Catalyzed Annulation of o-Acylanilines with Alkoxyheteroarenes: Synthesis of Heteroaryl[b]quinolines and Subsequent Transformation to Cryptolepine Derivatives

et al. 2018

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We disclose herein the first synthetic method that is capable of offering heteroaryl[b]quinolines (HA[b]Qs) with structural diversity, which include tricyclic and tetracyclic structures with (benzo)thienyl, (benzo)furanyl, and indolyl rings. The target HA[b]Q is addressed by the annulation of o-acylanilines and MeO–heteroarenes with the aid of an indium Lewis acid that effectively works to make two different types of the N–C and C–C bonds in one batch. A series of indolo[3,2-b]quinolines prepared here can be subsequently transformed to structurally unprecedented cryptolepine derivatives. Mechanistic studies showed that the N–C bond formation is followed by the C–C bond formation. The indium-catalyzed annulation reaction thus starts with the nucleophilic attack of the NH2 group of o-acylanilines to the MeO-connected carbon atom of the heteroaryl ring in an SNAr fashion, and thereby the N–C bond is formed. The resulting intermediate then cyclizes to make the C–C bond through the nucleophilic attack of the heteroaryl-ring-based carbon atom to the carbonyl carbon atom, providing the HA[b]Q after aromatizing dehydration.

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2-Benzyliden-2H-thieto[3,2-b]quinoline: a new heterocycle and its rearrangement to 2-phenylthieno[3,2-b]quinoline

Cited by 9 publications

References 14 publications

Recent progress on the chemistry of thieno[3,2‐b]quinoline derivatives (part III)

Recent progress on the chemistry of thieno[3,2‐b]quinoline derivatives (part III)

Aldo‐X Bifunctional Building Blocks for the Synthesis of Heterocycles

Indium-Catalyzed Annulation of o-Acylanilines with Alkoxyheteroarenes: Synthesis of Heteroaryl[b]quinolines and Subsequent Transformation to Cryptolepine Derivatives

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