New synthetic methodology for construction of the 3,4-dihydroisoquinolinone skeleton: A key structure for isoquinoline alkaloids

Date

2011-12-01

Author

Mujde, Berk
Ozcan, Sevil
Balcı, Metin

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We hereby report a new method for preparation of 3,4-dihydroisoquinolin-1(2H)-one as well as isoquinolin-1(2H)-one skeleton starting from the methyl 2-(3-methoxy-3-oxopropyl) benzoate. The ester functionality, adjacent to the methylene, was regiospecifically converted to the desired acyl azide. The isocyanate was transformed into the monoisocyanate by Curtius rearrangement followed by trapping with aniline. The formed urea derivative was cyclized with NaH to give a 3,4-dihydroisoquinolin-1(2H)-one derivative. Incorporation of a double bond into the six-membered ring followed by removal of the substituent resulted in the formation of isoquinolin-1(2H)-one skeleton. (C) 2011 Phytochemical Society of Europe. Published by Elsevier B. V. All rights reserved.

Subject Keywords

Biotechnology, Agronomy and Crop Science, Plant Science, Biochemistry

URI

https://hdl.handle.net/11511/49517

Journal

PHYTOCHEMISTRY LETTERS

DOI

https://doi.org/10.1016/j.phytol.2011.04.017

Collections

Graduate School of Natural and Applied Sciences, Article

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Citation Formats

B. Mujde, S. Ozcan, and M. Balcı, “New synthetic methodology for construction of the 3,4-dihydroisoquinolinone skeleton: A key structure for isoquinoline alkaloids,” PHYTOCHEMISTRY LETTERS, pp. 407–410, 2011, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/49517.