Rongalite-Induced Transition-Metal and Hydride-Free Reductive Aldol Reaction: A Rapid access to 3,3´- Disubstituted Oxindoles and Its Mechanistic Studies

Organic & Biomolecular Chemistry ◽

10.1039/d1ob02284a ◽

2022 ◽

Author(s):

Sivaparwathi Golla ◽

Naveenkumar Anugu ◽

Swathi Jalagam ◽

Hari Prasad Kokatla

Keyword(s):

Transition Metal ◽

Aldol Reaction ◽

Dual Role ◽

Biologically Active ◽

Mechanistic Studies ◽

Rapid Access ◽

Reductive Aldol ◽

Isatin Derivatives

A transition-metal and hydride-free reductive aldol reaction has been developed for the synthesis of biologically active 3,3´-disubstituted oxindoles from isatin-derivatives using rongalite. In this protocol, rongalite plays the dual role...

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A REVIEW ON RECENT ADVANCES IN CHEMISTRY, SYNTHESIS AND BIOLOGICAL APPLICATIONS OF ISATIN DERIVATIVES

Journal of Applied Pharmaceutical Sciences and Research ◽

10.31069/japsr.v1i2.13063 ◽

2018 ◽

pp. 16-22

Author(s):

Shukla PK ◽

Singh MP ◽

Patel R

Keyword(s):

Heterocyclic Compounds ◽

Biologically Active ◽

Biological Applications ◽

Plant Origin ◽

Recent Past ◽

Pharmacological Activities ◽

Naturally Occurring ◽

Recent Advances ◽

Biological Aspects ◽

Isatin Derivatives

Indole and its derivatives have engaged a unique place in the chemistry of nitrogen heterocyclic compounds. The recognition of the plant growthhormone, heteroauxin, the significant amino acids, tryptamine & tryptophan and anti-inflammatory drug, indomethacine are the imperativederivatives of indole which have added stimulus to this review work. Isatin (1H-indole-2,3-dione), an indole derivative of plant origin. Althoughit is a naturally occurring compound, but was synthesized by Erdmann and Laurent in 1840 before it was found in nature. Isatin is a versatileprecursor for many biologically active molecules and its diversified nature makes it a versatile substrate for further modifications. It is concernedin many pharmacological activities like anti-malarial, antiviral, anti-allergic, antimicrobial etc; isatin and its derivatives have been also found todemonstrate promising outcomes against various cancer cell lines. This review provides a brief overview on the recent advances and futureperspectives on chemistry and biological aspects of isatin and its derivatives reported in the recent past.

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ChemInform Abstract: Asymmetric Synthesis Catalyzed by Chiral Ferrocenylphosphine- Transition Metal Complexes. Part 10. Gold(I)-Catalyzed Asymmetric Aldol Reaction of Isocyanoacetate.

ChemInform ◽

10.1002/chin.199230044 ◽

2010 ◽

Vol 23 (30) ◽

pp. no-no

Author(s):

T. HAYASHI ◽

M. SAWAMURA ◽

Y. ITO

Keyword(s):

Transition Metal ◽

Metal Complexes ◽

Asymmetric Synthesis ◽

Transition Metal Complexes ◽

Aldol Reaction ◽

Asymmetric Aldol ◽

Asymmetric Aldol Reaction

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Transition-Metal-Free Boryl Substitution Using Silylboranes and Alkoxy Bases

Synlett ◽

10.1055/s-0036-1588772 ◽

2017 ◽

Vol 28 (11) ◽

pp. 1258-1267 ◽

Cited By ~ 2

Author(s):

Hajime Ito ◽

Eiji Yamamoto ◽

Satoshi Maeda ◽

Tetsuya Taketsugu

Keyword(s):

Transition Metal ◽

Functional Group ◽

Experimental Studies ◽

Transition Metal Catalysts ◽

Alkyl Halides ◽

Aryl Halides ◽

Nucleophilic Attack ◽

Important Class ◽

Mechanistic Studies ◽

Induced Reaction

Silylboranes are used as borylation reagents for organohalides in the presence of alkoxy bases without transition-metal catalysts. PhMe2Si–B(pin) reacts with a variety of aryl, alkenyl, and alkyl halides, including sterically hindered examples, to provide the corresponding organoboronates in good yields with high borylation/silylation ratios, showing good functional group compatibility. Halogenophilic attack of a silyl nucleophile on organohalides, and subsequent nucleophilic attack on the boron electrophile are identified to be crucial, based on the results of extensive theoretical and experimental studies. This borylation reaction is further applied to the first direct dimesitylboryl (BMes2) substitution of aryl halides using Ph2MeSi–BMes2 and Na(O-t-Bu), affording aryldimesitylboranes, which are regarded as an important class of compounds for organic materials.1 Introduction2 Boryl Substitution of Organohalides with PhMe2Si–B(pin)/Alkoxy Bases3 Mechanistic Investigations4 DFT Mechanistic Studies Using an Artificial Force Induced Reaction (AFIR) Method5 Dimesitylboryl Substitution of Aryl Halides with Ph2MeSi–BMes2/Na(O-t-Bu)6 Conclusion

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