Synthesis of Ring-Fused 1-Benzazepines via [1,5]-Hydride Shift/7-Endo Cyclization Sequences
- PMID: 28234485
- DOI: 10.1021/acs.orglett.7b00184
Synthesis of Ring-Fused 1-Benzazepines via [1,5]-Hydride Shift/7-Endo Cyclization Sequences
Abstract
Synthesis of 1-benzazepines has been achieved via a [1,5]-hydride shift/7-endo cyclization sequence. The focus of this research is a direct transformation of 2-(aryl)cyclopropane 1,1-diester derivatives into 1-benzazepines using a cyclopropane moiety as the hydride acceptor in internal redox reactions.
Similar articles
-
Enantioselective one-pot synthesis of ring-fused tetrahydroquinolines via aerobic oxidation and 1,5-hydride transfer/cyclization sequences.Org Lett. 2014 Oct 17;16(20):5374-7. doi: 10.1021/ol502575f. Epub 2014 Oct 3. Org Lett. 2014. PMID: 25280134
-
Aryl Radical Endo Cyclization of Enamidines. Selective Preparation of Trans and Cis Fused Octahydrobenzo[f]quinolines.J Org Chem. 1998 Jan 9;63(1):84-91. doi: 10.1021/jo971158d. J Org Chem. 1998. PMID: 11674046
-
Expeditious construction of a carbobicyclic skeleton via sp3-C-H functionalization: hydride shift from an aliphatic tertiary position in an internal redox process.J Am Chem Soc. 2011 Mar 2;133(8):2424-6. doi: 10.1021/ja110520p. Epub 2011 Feb 9. J Am Chem Soc. 2011. PMID: 21306120
-
Intramolecular redox reaction for the synthesis of N-aryl pyrroles catalyzed by Lewis acids.Org Biomol Chem. 2014 Dec 21;12(47):9716-9. doi: 10.1039/c4ob02009j. Epub 2014 Oct 29. Org Biomol Chem. 2014. PMID: 25351145
-
Controllable Synthesis of N-Heterocycles via Hydride Transfer Strategy-Enabled Formal [5 + 1] and [5 + 2] Cyclizations.Org Lett. 2024 Jan 12;26(1):332-337. doi: 10.1021/acs.orglett.3c03986. Epub 2023 Dec 28. Org Lett. 2024. PMID: 38153999
Cited by
-
α-Functionalization of Cyclic Secondary Amines: Lewis Acid Promoted Addition of Organometallics to Transient Imines.J Am Chem Soc. 2019 Jun 5;141(22):8778-8782. doi: 10.1021/jacs.9b04325. Epub 2019 May 24. J Am Chem Soc. 2019. PMID: 31117670 Free PMC article.
-
Borane-catalyzed cascade Friedel-Crafts alkylation/[1,5]-hydride transfer/Mannich cyclization to afford tetrahydroquinolines.Chem Sci. 2021 Dec 20;13(3):775-780. doi: 10.1039/d1sc05629h. eCollection 2022 Jan 19. Chem Sci. 2021. PMID: 35173942 Free PMC article.
-
Redox-Annulations of Cyclic Amines with 2-(2-Oxoethyl)malonates.Org Lett. 2018 Jul 6;20(13):4090-4093. doi: 10.1021/acs.orglett.8b01642. Epub 2018 Jun 25. Org Lett. 2018. PMID: 29939750 Free PMC article.
-
Redox-triggered cascade dearomative cyclizations enabled by hexafluoroisopropanol.Chem Sci. 2018 Sep 13;9(43):8253-8259. doi: 10.1039/c8sc03339k. eCollection 2018 Nov 21. Chem Sci. 2018. PMID: 30542574 Free PMC article.
-
Redox-Annulations of Cyclic Amines with Electron-Deficient o-Tolualdehydes.Org Lett. 2019 Mar 15;21(6):1845-1848. doi: 10.1021/acs.orglett.9b00438. Epub 2019 Mar 6. Org Lett. 2019. PMID: 30840479 Free PMC article.
Publication types
LinkOut - more resources
Full Text Sources
Other Literature Sources