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Journal ArticleDOI

Tandem Strecker/C(sp3)–H amination reactions for the construction of cyanide-functionalized imidazo[1,5-a]pyridines with NH4SCN as a cyanating agent

TL;DR: An I2O5-mediated multicomponent reaction that allows the single-step construction of cyano-functionalized imidazo[1,5-a]pyridines with molecular diversity was realized for the first time.
Abstract: An I2O5 promoted tandem Strecker/C(sp3)–H amination reaction of pyridine-2-carboxaldehydes, benzylamines and NH4SCN has been reported. This multicomponent reaction that allows the single-step construction of biologically important cyano-functionalized imidazo[1,5-a]pyridines with molecular diversity was realized for the first time. Moreover, the use of safe and easy-to-handle NH4SCN as a surrogate cyanating agent makes this protocol appealing for potential applications.
Citations
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TL;DR: An I2-mediated [3 + 2] annulation of methyl-azaarenes with alkyl 2-isocyanoacetates or amino acid ester hydrochlorides has been demonstrated.
Abstract: An I2-mediated [3 + 2] annulation of methyl-azaarenes with alkyl 2-isocyanoacetates or amino acid ester hydrochlorides has been demonstrated. This strategy involves the C≡N cleavage of isocyanides and can selectively...

7 citations

Journal ArticleDOI
TL;DR: In this paper , the authors summarize the advances in this research field since 2019 and discuss the challenges and future developments in the intramolecular electrochemical C-H aminations.
Abstract: N-heterocycles are key structural units in many drugs, biologically interesting molecules and functional materials. To avoid the residues of metal catalysts, the construction of N-heterocycles under metal-free conditions has attracted much research attention in academia and industry. Among them, the intramolecular electrochemical C-H aminations arguably constitute environmentally friendly methodologies for the metal-free construction of N-heterocycles, mainly due to the direct use of clean electricity as the redox agents. With the recent renaissance of organic electrosynthesis, the intramolecular electrochemical C-H aminations have undergone much progress in recent years. In this article, we would like to summarize the advances in this research field since 2019. The emphasis is placed on the reaction design and mechanistic insight. The challenges and future developments in the intramolecular electrochemical C-H aminations are also discussed.

3 citations

Journal ArticleDOI
TL;DR: In this article , the reaction of arylaldehydes and arylamines with NH4SCN in the presence of TBHP led to a divergent Strecker synthesis of aminonitriles and iminonite.
Abstract: The reaction of arylaldehydes and arylamines with NH4SCN in the presence of TBHP led to a divergent Strecker synthesis of aminonitriles and iminonitriles. The striking feature of this modified Strecker...

1 citations

References
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Journal ArticleDOI
Yujiro Hayashi1
TL;DR: This review describes the importance and usefulness of pot-economy and one-pot reactions in current synthetic organic chemistry.
Abstract: The one-pot synthesis of a target molecule in the same reaction vessel is widely considered to be an efficient approach in synthetic organic chemistry. In this review, the characteristics and limitations of various one-pot syntheses of biologically active molecules are explained, primarily involving organocatalytic methods as key tactics. Besides catalysis, the pot-economy concepts presented herein are also applicable to organometallic and organic reaction methods in general.

686 citations

Journal ArticleDOI
TL;DR: A critical review of the important developments in palladium-catalyzed cyanation of Ar-X from 2000 until 2010 concludes that this methodology is the most popular for preparation of substituted aromatic nitriles.
Abstract: The palladium-catalyzed cyanation of Ar–X (X = I, Br, Cl, OTf, and H) allows for an efficient access towards benzonitriles. After its discovery in 1973 and following significant improvements in recent decades, this methodology has become nowadays the most popular for preparation of substituted aromatic nitriles. In this critical review, we summarize the important developments in this area from 2000 until 2010 (151 references).

548 citations