124394-17-8Relevant academic research and scientific papers
Phosphazene Superbase-Mediated Regio- and Stereoselective Iodoaminocyclization of 2-(1-Alkynyl)benzamides for the Synthesis of Isoindolin-1-ones
Mehta, Saurabh,Brahmchari, Dhirendra
, p. 5492 - 5503 (2019/05/10)
Phosphazene superbase P4-t-Bu mediated iodoaminocyclization of 2-(1-alkynyl)benzamides is reported. The reaction works under ambient conditions and instantaneously results in the synthesis of isoindolin-1-ones in 65-97% yields, in a regio- and stereoselective manner. The exclusive formation of products with Z-geometry (across the exo C?C bond) has been confirmed through X-ray crystallography. The methodology also provides an easy access to aristolactams, an important class of natural products. This has been successfully demonstrated by synthesizing two aristolactam derivatives (including Cepharanone B).
Regio- and Stereoselective Synthesis of Isoindolin-1-ones through BuLi-Mediated Iodoaminocyclization of 2-(1-Alkynyl)benzamides
Brahmchari, Dhirendra,Verma, Akhilesh K.,Mehta, Saurabh
supporting information, p. 3339 - 3347 (2018/03/23)
A simple and straightforward synthesis of isoindolin-1-ones is reported. Exclusive N-cyclization of the amide functional group, an ambident nucleophile, was accomplished for the cyclization of 2-(1-alkynyl)benzamides using n-BuLi-I2/ICl. The methodology works with the primary amide and affords the desired isoindolinones in yields of 38-94%. Interestingly, the isolated products exhibit a Z-stereochemistry across the C=C double bond. The reaction mechanism involving the formation of either a vinylic anion or an intimate ion pair intermediate is proposed.
Concise one-pot tandem synthesis of indoles and isoquinolines from amides
Okamoto, Noriko,Miwa, Yoshihisa,Minami, Hideki,Takeda, Kei,Yanada, Reiko
supporting information; experimental part, p. 9693 - 9696 (2010/04/28)
Heterocyclic hot pot: Platinum[II]-catalyzed syntheses of indoles and isoquinolines from isocyanates, which are derived from a Hofmann-type rearrangement of amides using a hypervalent iodine reagent, are described. C2-symmetric macrocyclic bis[indole]s ca
