Electrochemical Dearomative Dihydroxylation and Hydroxycyclization of Indoles
International audience
International audience
Published in Topics in Current Chemistry
Heterocyclic compounds having a nitrogen atom in the ring exhibit very interesting biological activities. Indole is the core structure of many bioactive compounds owing to its high affinity to bind with most biological targets. Indole is an electron-rich compound and generally prefers electrophilic rather than nucleophilic substitution. Hence, many...
Published in Bioorganic chemistry
Indoline framework is often perpended as a privileged heterocycle present in medicinally valuable compounds of natural and synthetic origin. This review article presents the rational approaches/strategies employed for the design of anticancer indolines along with the structure activity relationship and mechanistic insights revealed in the in-vitro ...
Published in Angewandte Chemie (International ed. in English)
A biomimetic route to farnesyl pyrophosphate and dimethyl orsellinic acid (DMOA)-derived meroterpenoid scaffolds has yet to be reported despite great interest from the chemistry and biomedical research communities. A concise synthetic route with the potential to access DMOA-derived meroterpenoids is highly desirable to create a library of related c...
In this work, we have described the development of new transformations using bio-based renewable methyl coumalate as feedstock. An iron and copper catalyzed one-pot sequential double alkyl-alkyl or alkyl-hydride 1,6-addition with methyl coumalate was described. We then described an efficient synthesis of tetrasubstituted 2H-pyrans under mild condit...
Published in Molecular Diversity
Reaction of amidrazones 1a–1i with (1,5-dihydro-3-methyl-5-oxo-1-phenyl-4H-pyrazol-4-ylidene)propanedinitrile (2) in ethyl acetate solution in one-step reaction led to the formation of unprecedented pyrazolo[4,3-c][1,2,4]triazino[4,5-a]quinolin-4(5H)-ones 3a–3g along with pyrazolo[4,3-c][1,2,4]triazino[4,5-a]quinolin-12b-oles 3h–3m in moderate to e...
The need for metal-free environmentally benign catalysts has provided a strong impetus toward the emergence of hypercoordinate iodine reagents. At this stage of development, molecular insights on the mechanism and origin of stereo selectivity are quite timely. In this study, the origin of stereoinduction in a class of iodoresorcinol-based chiral hy...
Published in The Journal of organic chemistry
Synthesis of a tetracyclic ring system (BCDE) of atropurpuran is described. Oxidative dearomatization, cycloaddition of spiroepoxycyclohexa-2,4-dienone, radical cyclization, and a tandem oxidation-aldol-oxidation are the key features of our methodology.
Published in Journal of Molecular Modeling
The Pd-catalyzed dearomatization of naphthalene allyl chloride with allyltributylstannane has been investigated using density functional theory (DFT) calculations at the B3LYP level. The calculations indicate that the (ŋ1-allyl)(ŋ3-allyl)Pd(PH3) complex is responsible for the formation of ortho-dearomatized product. Moreover it is easy to produce t...
Published in European journal of organic chemistry
An exploration of an abiotic approach to spirocalcaridines A and B is described centered on electrophile-induced dearomatizing spirocyclization of aryl enyne derivatives. Elaboration of the α-iodoenone via an Ullmann-like, copper-catalyzed amidation provided a formamide which upon treatment with methylamine undergoes a dienol-arene rearrangement, p...