Guntreddi, Tirumaleswararao ; Shankar, Majji ; Kommu, Nagarjuna ; Sahoo, Akhila K. (2019) Construction of Pyranoisoquinolines via Ru(II)-Catalyzed Unsymmetrical Double Annulation of N-Methoxybenzamides with Unactivated Alkynes Journal of Organic Chemistry, 84 (20). pp. 13033-13044. ISSN 0022-3263
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Official URL: http://doi.org/10.1021/acs.joc.9b01878
Related URL: http://dx.doi.org/10.1021/acs.joc.9b01878
Abstract
A ruthenium (Ru)-catalyzed double annulation of easily accessible N-methoxybenzamide derivatives with unactivated alkynes for the synthesis of unusual 6,6-fused pyranoisoquinolines is described. Both ortho-C–H bonds of arenes and the N- and O-moieties of N-methoxybenzamides are involved in the construction of four [(C–C)–(C–N) and (C–C)–(C–O)] bonds in one step under single catalytic conditions. The unsymmetrical annulation of N-methoxybenzamides with two distinct alkynes is also demonstrated. The oxidizable directing group N-methoxyamine (NHOMe) assists the unsymmetrical double annulations of arenes [that use both N- and O-heteroatoms] in a single operation. This synthetic method features excellent substrate scope and tolerates a wide range of functional groups. Peripheral modification of pyranoisoquinolines for the construction of complex heterocyclic compounds is also demonstrated.
Item Type: | Article |
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Source: | Copyright of this article belongs to American Chemical Society. |
ID Code: | 121772 |
Deposited On: | 22 Jul 2021 07:16 |
Last Modified: | 22 Jul 2021 07:16 |
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