Convenient synthesis of a simple coumarin from salicylaldehyde and wittig reagent (III)1 1 T. Harayama, K. Nakatsuka, H. Nishioka, K. Murakami, N. Hayashida, and H. Ishii, Chem. Pharm. Bull., accepted.: Synthesis of nitrocoumarins

Takashi Harayama; Kazumitsu Nakatsuka; Hiromi Nishioka; Kyoko Murakami; Yukiko Ohmori; Yasuo Takeuchi; Hisashi Ishii; Kazuhiro Kenmotsu

doi:10.3987/COM-94-6910

Convenient synthesis of a simple coumarin from salicylaldehyde and wittig reagent (III)¹ 1 T. Harayama, K. Nakatsuka, H. Nishioka, K. Murakami, N. Hayashida, and H. Ishii, Chem. Pharm. Bull., accepted. Synthesis of nitrocoumarins

Takashi Harayama, Kazumitsu Nakatsuka, Hiromi Nishioka, Kyoko Murakami, Yukiko Ohmori, Yasuo Takeuchi, Hisashi Ishii, Kazuhiro Kenmotsu

Research output: Contribution to journal › Article › peer-review

23 Citations (Scopus)

Abstract

Reaction of nitrosalicylaldehydes (1) with carbethoxymethylenetri-phenylphosphorane in Et₂NPh, in Ph₂O, and in the absence of solvent (neat) at 210-215 °C was investigated. Reaction of 3-nitrosalicylaldehyde (1d) in Et₂NPh afforded the benzoxazole (6) and the aminocoumarin (3e) along with the expected coumarin (3d). It was clarified that the origin of carbon-unit introduced for the formation of the benzoxazole ring came from the alkyl group of solvent.

Original language	English
Pages (from-to)	2729-2738
Number of pages	10
Journal	Heterocycles
Volume	38
Issue number	12
DOIs	https://doi.org/10.3987/COM-94-6910
Publication status	Published - Dec 1 1994

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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Harayama, T., Nakatsuka, K., Nishioka, H., Murakami, K., Ohmori, Y., Takeuchi, Y., Ishii, H., & Kenmotsu, K. (1994). Convenient synthesis of a simple coumarin from salicylaldehyde and wittig reagent (III)¹ 1 T. Harayama, K. Nakatsuka, H. Nishioka, K. Murakami, N. Hayashida, and H. Ishii, Chem. Pharm. Bull., accepted. Synthesis of nitrocoumarins. Heterocycles, 38(12), 2729-2738. https://doi.org/10.3987/COM-94-6910

Convenient synthesis of a simple coumarin from salicylaldehyde and wittig reagent (III)¹ 1 T. Harayama, K. Nakatsuka, H. Nishioka, K. Murakami, N. Hayashida, and H. Ishii, Chem. Pharm. Bull., accepted. Synthesis of nitrocoumarins. / Harayama, Takashi; Nakatsuka, Kazumitsu; Nishioka, Hiromi; Murakami, Kyoko; Ohmori, Yukiko; Takeuchi, Yasuo; Ishii, Hisashi; Kenmotsu, Kazuhiro.

In: Heterocycles, Vol. 38, No. 12, 01.12.1994, p. 2729-2738.

Research output: Contribution to journal › Article › peer-review

Harayama, T, Nakatsuka, K, Nishioka, H, Murakami, K, Ohmori, Y, Takeuchi, Y, Ishii, H & Kenmotsu, K 1994, 'Convenient synthesis of a simple coumarin from salicylaldehyde and wittig reagent (III)¹ 1 T. Harayama, K. Nakatsuka, H. Nishioka, K. Murakami, N. Hayashida, and H. Ishii, Chem. Pharm. Bull., accepted. Synthesis of nitrocoumarins', Heterocycles, vol. 38, no. 12, pp. 2729-2738. https://doi.org/10.3987/COM-94-6910

Harayama T, Nakatsuka K, Nishioka H, Murakami K, Ohmori Y, Takeuchi Y et al. Convenient synthesis of a simple coumarin from salicylaldehyde and wittig reagent (III)¹ 1 T. Harayama, K. Nakatsuka, H. Nishioka, K. Murakami, N. Hayashida, and H. Ishii, Chem. Pharm. Bull., accepted. Synthesis of nitrocoumarins. Heterocycles. 1994 Dec 1;38(12):2729-2738. https://doi.org/10.3987/COM-94-6910

Harayama, Takashi ; Nakatsuka, Kazumitsu ; Nishioka, Hiromi ; Murakami, Kyoko ; Ohmori, Yukiko ; Takeuchi, Yasuo ; Ishii, Hisashi ; Kenmotsu, Kazuhiro. / Convenient synthesis of a simple coumarin from salicylaldehyde and wittig reagent (III)¹ 1 T. Harayama, K. Nakatsuka, H. Nishioka, K. Murakami, N. Hayashida, and H. Ishii, Chem. Pharm. Bull., accepted. Synthesis of nitrocoumarins. In: Heterocycles. 1994 ; Vol. 38, No. 12. pp. 2729-2738.

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AB - Reaction of nitrosalicylaldehydes (1) with carbethoxymethylenetri-phenylphosphorane in Et2NPh, in Ph2O, and in the absence of solvent (neat) at 210-215 °C was investigated. Reaction of 3-nitrosalicylaldehyde (1d) in Et2NPh afforded the benzoxazole (6) and the aminocoumarin (3e) along with the expected coumarin (3d). It was clarified that the origin of carbon-unit introduced for the formation of the benzoxazole ring came from the alkyl group of solvent.

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Convenient synthesis of a simple coumarin from salicylaldehyde and wittig reagent (III)1 1 T. Harayama, K. Nakatsuka, H. Nishioka, K. Murakami, N. Hayashida, and H. Ishii, Chem. Pharm. Bull., accepted. Synthesis of nitrocoumarins

Abstract

ASJC Scopus subject areas

Access to Document

Cite this

Convenient synthesis of a simple coumarin from salicylaldehyde and wittig reagent (III)¹ 1 T. Harayama, K. Nakatsuka, H. Nishioka, K. Murakami, N. Hayashida, and H. Ishii, Chem. Pharm. Bull., accepted. Synthesis of nitrocoumarins