Organocatalytic one-pot asymmetric synthesis of 4H,5H-pyrano[2,3-c]pyrazoles
- PMID: 22852800
- DOI: 10.1021/ol301983f
Organocatalytic one-pot asymmetric synthesis of 4H,5H-pyrano[2,3-c]pyrazoles
Abstract
An efficient one pot asymmetric synthesis of tetrahydropyrano[2,3-c]pyrazoles has been developed. This class of biologically active heterocycles can be obtained via a secondary amine catalyzed asymmetric Michael/Wittig/oxa-Michael reaction sequence. Remarkably, the title compounds were accessible in good to very good yields and very good to excellent enantioselectivities after a single purification step.
Similar articles
-
One-pot formation of chiral polysubstituted 3,4-dihydropyrans via a novel organocatalytic domino sequence involving alkynal self-condensation.Org Lett. 2013 Jan 4;15(1):204-7. doi: 10.1021/ol3032285. Epub 2012 Dec 21. Org Lett. 2013. PMID: 23259735
-
Synthesis and molluscicidal activity of new cinnoline and pyrano [2,3-c]pyrazole derivatives.Arch Pharm (Weinheim). 2006 Aug;339(8):456-60. doi: 10.1002/ardp.200600057. Arch Pharm (Weinheim). 2006. PMID: 16795107
-
Effective and novel enantioselective preparation of pyranopyrazoles and pyranocoumarins that is catalyzed by a quinine-derived primary amine.Org Biomol Chem. 2016 Jan 14;14(2):623-630. doi: 10.1039/c5ob01656h. Org Biomol Chem. 2016. PMID: 26540619
-
Recent developments in utility of green multi-component reactions for the efficient synthesis of polysubstituted pyrans, thiopyrans, pyridines, and pyrazoles.Mol Divers. 2015 Aug;19(3):625-51. doi: 10.1007/s11030-015-9594-2. Epub 2015 Apr 17. Mol Divers. 2015. PMID: 25894364 Review.
-
Cycloadditions and condensations as essential tools in spiropyrazoline synthesis.Eur J Med Chem. 2013 May;63:347-77. doi: 10.1016/j.ejmech.2013.01.059. Epub 2013 Mar 6. Eur J Med Chem. 2013. PMID: 23517727 Review.
Cited by
-
Substituted Pyrazoles and Their Heteroannulated Analogs-Recent Syntheses and Biological Activities.Molecules. 2021 Aug 18;26(16):4995. doi: 10.3390/molecules26164995. Molecules. 2021. PMID: 34443583 Free PMC article. Review.
-
Recent Advances in Organocatalyzed Domino C-C Bond-Forming Reactions.Molecules. 2017 Dec 23;23(1):33. doi: 10.3390/molecules23010033. Molecules. 2017. PMID: 29295474 Free PMC article. Review.
-
Cerium ammonium nitrate (CAN)-catalyzed four-component one-pot synthesis of multi-substituted pyrano[2,3-c] pyrazoles under ultrasound irradiation.Mol Divers. 2013 Nov;17(4):693-700. doi: 10.1007/s11030-013-9465-7. Epub 2013 Aug 6. Mol Divers. 2013. PMID: 23918005
-
Cascade annulation reaction (CAR): highly diastereoselective synthesis of pyranopyrazole scaffolds.RSC Adv. 2020 May 19;10(32):19003-19007. doi: 10.1039/d0ra03400b. eCollection 2020 May 14. RSC Adv. 2020. PMID: 35518344 Free PMC article.
-
Racemic hemiacetals as oxygen-centered pronucleophiles triggering cascade 1,4-addition/Michael reaction through dynamic kinetic resolution under iminium catalysis. Development and mechanistic insights.Chem Sci. 2017 Apr 1;8(4):2904-2913. doi: 10.1039/c7sc00009j. Epub 2017 Jan 30. Chem Sci. 2017. PMID: 28451356 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources