Indium(III)-Catalyzed Tandem Reaction with Alkynylbenzaldehydes and Alkynylanilines to Heteroaromatic Compounds

Yanada, Reiko; Hashimoto, Kana; Tokizane, Rie; Miwa, Yoshihisa; Minami, Hideki; Yanada, Kazuo; Ishikura, Minoru; Takemoto, Yoshiji

doi:10.1021/jo800474c

Cited by 89 publications

(39 citation statements)

References 40 publications

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“…Compared to the stepwise approach, cascade reactions represent an attractive strategy in synthesis because multiple bond-forming and -cleaving events can be combined into a single reaction operation. Recently, transition-metal-catalyzed cascade processes have received significant attention [ 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 ]. Among these transition metals, silver salts have long been believed to have low catalytic efficiency, and most commonly served as either co-catalysts or weak Lewis acids [ 20 ].…”

Section: Introductionmentioning

confidence: 99%

‘One-pot’ Synthesis of Dihydrobenzo[4,5][1,3]oxazino[2,3-a] isoquinolines via a Silver(I)-Catalyzed Cascade Approach

et al. 2013

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Section: Introductionmentioning

confidence: 99%

‘One-pot’ Synthesis of Dihydrobenzo[4,5][1,3]oxazino[2,3-a] isoquinolines via a Silver(I)-Catalyzed Cascade Approach

et al. 2013

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“…It has been reported recently that In(OTf) 3 can act as a efficient catalyst for the synthesis of phenanthridines through cyclizations of phenylacetylenecarbaldehydes with ortho alkynylanilines. [98] Phenylacetylene-carbaldehydes bearing electron-withdrawing groups on their aromatic rings are better substrates than those with electron-donating groups. The application of this methodology to various substrates is shown in Table 9.…”

Section: Synthesis Of Phenanthridinesmentioning

confidence: 99%

Recent Developments in Indium Metal and Its Salts in Organic Synthesis

et al. 2010

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Indium and its salts have emerged as promising catalysts for effecting various functional group transformations in last two decades. There are a great number of reported reactions involving indium reagents; the versatility and the applicability of these reactions makes it a hot field to explore, and it attracts much interest from organic chemists. The development of indium reagents in C–C bond‐formation reactions, coupling reactions, asymmetric synthesis in the presence of chiral‐metal ligand complexes, etc. has made this field more attractive. Indium salts have pronounced Lewis acid character and are also attractive because of their moderate stability to water. Here we highlight developments in indium chemistry reported in the last eight years.

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“…In addition to this, we have also developed several new C(heteroaryl)–C bond-forming reactions by reacting alkynes [ 55 , 56 , 57 ] or carbonyl compounds [ 58 , 59 , 60 ] with heteroarenes. All of these reactions are effectively catalyzed by a salt of an indium(III) Lewis acid, which has been also employed for various organic transformations by other research groups [ 61 , 62 , 63 , 64 , 65 , 66 , 67 , 68 , 69 , 70 , 71 ]. We therefore envisaged that conducting the two different types of reactions in a tandem fashion would be a new methodology of the strategy b to offer the HA[ b ]Q in an easy way, thereby also leading to the further expansion of our indium-based technology.…”

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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Indium(III)-Catalyzed Tandem Reaction with Alkynylbenzaldehydes and Alkynylanilines to Heteroaromatic Compounds

Abstract: Starting from ortho-alkynylbenzaldehydes and ortho-alkynylanilines, In(OTf)3-catalyzed synthesis of ring-condensed heteroaromatic compounds was developed via a domino intramolecular nucleophilic attack/intermolecular cycloaddition/dehydration reaction.

Cited by 89 publications

References 40 publications

‘One-pot’ Synthesis of Dihydrobenzo[4,5][1,3]oxazino[2,3-a] isoquinolines via a Silver(I)-Catalyzed Cascade Approach

‘One-pot’ Synthesis of Dihydrobenzo[4,5][1,3]oxazino[2,3-a] isoquinolines via a Silver(I)-Catalyzed Cascade Approach

Recent Developments in Indium Metal and Its Salts in Organic Synthesis

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

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