Synthesis of Advanced Intermediates of Lennoxamine Analogues

Sarang, Prajakta S.; Yadav, Arun A.; Patil, Pramod; Krishna, U. Murali; Trivedi, Gaurav; Salunkhe, Manikrao M.

doi:10.1055/s-2007-965950

Cited by 4 publications

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“…Our findings can also explain the results published by Trivedi and Salunkhe a few years ago. 44 Various isoindolin-1-ones (advanced intermediates of the (±)-lennoxamine alkaloid) retaining the carboxylic acid moiety were synthesized.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 2-Tetrazolylmethyl-isoindolin-1-ones via a One-Pot Ugi-Azide/(N-Acylation/exo-Diels–Alder)/Dehydration Process

et al. 2016

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A series of fifteen 2-tetrazolylmethyl-isoindolin-1-one linked-type bis-heterocycles were synthesized in 10–76% yields under mild conditions via a one-pot Ugi-azide/(N - acylation/ exo -Diels–Alder)/dehydration process from furan-2-ylmethanamine, aldehydes, isocyanides, azidotrimethylsilane, and maleic anhydride. Density functional theory calculations were performed using the polarizable continuum model (toluene)-M06-2X-D3/6-311+G(d)//M06-2X-D3/6-31G(d) level of theory to obtain the full energy profile when investigating over eight possible pathways. An anthracene-containing analogue displayed a distribution of its highest occupied molecular orbital–lowest unoccupied molecular orbital throughout both cyclic moieties.

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Section: Resultsmentioning

confidence: 99%