85796-90-3Relevant academic research and scientific papers
Catalytic Acceptorless Dehydrogenation of Amino Alcohols and 2-Hydroxybenzyl Alcohols for Annulation Reaction under Neutral Conditions
Pandey, Akanksha M.,Digrawal, Naveen Kumar,Mohanta, Nirmala,Jamdade, Akash Bandu,Chaudhari, Moreshwar B.,Bisht, Girish Singh,Gnanaprakasam, Boopathy
, p. 8805 - 8828 (2021/07/20)
A base-free and acceptorless Ru-catalyzed dehydrogenative approach has been developed for the synthesis ofN-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 H2are the only byproducts in this domino process. Moreover, RuH2CO(PPh3)3-catalyzed C3-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.
Synthesis of 3,1-benzoxazines and tetrahydroquinazolines from o-aminobenzyl alcohol and o-aminobenzyl amine - Semi-empirical MO calculations
Lessel
, p. 329 - 336 (2007/10/02)
o-Aminobenzyl alcohol (4) reacts with aldehydes and ketones to the 3,1-benzoxazines 20a/b and 22a/b, whereas the enamine derivatives 24a-c are formed from β-diketones. The isosteric o-amino-benzylamine (1) gives tetrahydroquinazolines 11a/b and 14b as het
