Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 13, Pages 8805-8828Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00714
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Funding
- SERB [CRG/2018/003935]
- Council of Scientific and Industrial Research, India [02(0296/17/EMR-II)]
- IISER-Pune
- CSIR
- SERB
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A base-free and acceptorless Ru-catalyzed dehydrogenative approach has been developed for the synthesis of N-heterocycles and O-heterocycles, which is applicable for the preparation of biologically important scaffolds.
A base-free and acceptorless Ru-catalyzed dehydro-genative approach has been developed for the synthesis of N-heterocycles by using 1,3-dicarbonyls and amino alcohols through a domino sequential enamine formation and intramolecular oxidative cyclization strategy. This unified approach is also applicable for the synthesis of O-heterocycles involving 2-hydroxybenzyl alcohol as a coupling reactant via consecutive C-alkylation and intramolecular cyclization steps. The present protocol is general for the synthesis of varieties of biologically important scaffolds, such as tetrahydro-4H-indol-4-one, 3,4-dihydroacridin-1(2H)-one, and tetrahydro-1H-xanthen-1-ones derivatives using a single catalytic system, viz. RuH2CO(PPh3)(3). Environmentally benign H2O and H-2 are the only byproducts in this domino process. Moreover, RuH2CO(PPh3)(3)-catalyzed C-3-alkylation of tetrahydro-4H-indol-4-one using alcohol as a alkylating partner is also described in this report. For the first time, a solvent-free gram-scale reaction for the acceptorless dehydrogenative annulation has been demonstrated. A plausible mechanism for the Ru-catalyzed base-free and acceptorless dehydrogenative annulation of amino alcohols or 2-hydroxybenzyl alcohols has been provided with several experimental investigations and spectroscopic evidence.
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