A P(III)‐mediated entry towards construction of C−N/C−S bond has been devised. The developed heterocyclization method was exercised for the synthesis of a diverse range of N,S‐heterocycles and ...related spiro molecules. P(NMe2)3 revealed the maximum efficacies under the aerobic reaction conditions and a spectrum of bis‐nucleophiles, and isothiocyanates were tolerated well to serve the access of manifold immense molecules.
A Phosphine-free and effective process has been expressed for the formulation of N,S-heterocycles following a C-N/C-S bond forming reactions. The described process operates through EDC-HCl-mediated ...heterocyclization of diverse isothiocyanates and bis-nucleophiles to deliver 1,3-thiazinone derivatives, which eliminates the use of hazardous reagents. The developed protocol was found applicable over a wide range of substrates in delivering N,S-heterocycles in excellent yields at room temperature and short reaction time.
An efficient and mild protocol was realized using 1,2‐diazoles and related heterocycles with cyclic and acyclic enones in presence of T3P ...(2,4,6‐tripropyl‐1,3,5,2,4,6‐trioxatriphosphorinane‐2,4,6‐trioxide) toward the regioselective formation of N‐cycloalkyl heterocycles at room temperature. The developed reaction conditions showcased good selectivity over a wide range of 1,2‐diazoles and enones by delivering N‐cycloalkyl heterocycles in excellent yields.
Keywords: 1,2-diazoles; aza-Michael addition; cyclic enones; N-cycloalkyl heterocycles; T3P-mediated An efficient and mild protocol was realized using 1,2-diazoles and related heterocycles with ...cyclic and acyclic enones in presence of T3P (2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide) toward the regioselective formation of N-cycloalkyl heterocycles at room temperature. The developed reaction conditions showcased good selectivity over a wide range of 1,2-diazoles and enones by delivering N-cycloalkyl heterocycles in excellent yields. Article Note: Funding information Science and Engineering Research Board, Grant/Award Numbers: CRG/2020/004509, ECR/2016/000337; Technical Education Quality Improvement Program, Phase-III, Grant/Award Number: Minor Research Grant CAPTION(S): Appendix S1: Supporting Information Byline: Saibabu Polina, V. P. Rama Kishore Putta, Raghuram Gujjarappa, Prasad Pralhad Pujar, Chandi C. Malakar
Abstract An expeditious strategy has been developed for the synthesis of diverse quinolines, indenoquinolines and acridines using KO t Bu‐mediated reaction conditions. The designed process utilizes ...2‐aminoaryl carbaldehydes/2‐aminoaryl ketones and methyl/methylene group containing ketones as readily available feedstock. The chemical transformation was affected at room temperature within a short duration of time to obtain diverse N ‐heterocycles yields up to 92 %. The established process also exhibits considerable functional group tolerance with an operational simplicity.
KOtBu mediates the reaction between 2‐amino arylcarbaldehydes and benzyl/alkyl cyanides toward the expeditious formation of 2‐aminoquinolines under transition‐metal‐free conditions. The described ...transformation proceeds through in‐situ generated enimine intermediate from benzyl/alkyl cyanides under KOtBu‐mediated reaction conditions. The substituted 2‐aminoquinolines were realized in excellent yields at room temperature and shorter reaction time. The designed process exhibits operational simplicity and broad functional group tolerance in delivering the products of high significance.
KOtBu‐mediated protocol has been described for the comprehensive synthesis of 2‐Aminoquinolines using benzyl/alkyl cyanides and 2‐amino arylcarbaldehydes. The developed domino reaction conditions holds good for wide range of substrates by giving the desired products in excellent yields at room temperature and shorter reaction time.
An expeditious strategy has been developed for the synthesis of diverse quinolines, indenoquinolines and acridines using KOtBu‐mediated reaction conditions. The designed process utilizes 2‐aminoaryl ...carbaldehydes/2‐aminoaryl ketones and methyl/methylene group containing ketones as readily available feedstock. The chemical transformation was affected at room temperature within a short duration of time to obtain diverse N‐heterocycles yields up to 92 %. The established process also exhibits considerable functional group tolerance with an operational simplicity.
A potassium tert‐butoxide mediated approach has been envisioned towards the synthesis of quinolines, indenoquinoline and acridines from their corresponding 2‐aminoaryl carbaldehydes/2‐aminoaryl ketones and methyl/methylene group containing ketones. The developed operational friendly reaction conditions hold good for wide range of substrates by delivering the desired products in good to excellent yields at room temperature and shorter reaction time.
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•Rarely explored substrates have been investigated towards saturated N-heterocycles.•Developed method exclude the use of P(III) reagents for reductive cyclization.•Alternate source of ...molecular carbon monoxide has been used as sole reducing agent.
Using Pd/HCOOCs as a surrogate reagents synthesis of saturated N-heterocycles was described from nitroaromatics as starting materials. The developed new reaction conditions exclude the generally used toxic reagents like carbon monoxide as deoxygenative agent. The developed protocol permits the synthesis privileged bioactive N-heterocyclic scaffolds in good yields and selectivity.
