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

Access to Document

10.3987/COM-94-6910

Fingerprint

Dive into the research topics of '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'. Together they form a unique fingerprint.

Cite this

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 et al.

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. doi: 10.3987/COM-94-6910

@article{6f9ae69fd39342008c4fbc684544d7db,

title = "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 = "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.",

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

year = "1994",

month = dec,

day = "1",

doi = "10.3987/COM-94-6910",

language = "English",

volume = "38",

pages = "2729--2738",

journal = "Heterocycles",

issn = "0385-5414",

publisher = "Japan Institute of Heterocyclic Chemistry",

number = "12",

}

TY - JOUR

T1 - 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.

T2 - Synthesis of nitrocoumarins

AU - Harayama, Takashi

AU - Nakatsuka, Kazumitsu

AU - Nishioka, Hiromi

AU - Murakami, Kyoko

AU - Ohmori, Yukiko

AU - Takeuchi, Yasuo

AU - Ishii, Hisashi

AU - Kenmotsu, Kazuhiro

PY - 1994/12/1

Y1 - 1994/12/1

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=0001030405&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0001030405&partnerID=8YFLogxK

U2 - 10.3987/COM-94-6910

DO - 10.3987/COM-94-6910

M3 - Article

AN - SCOPUS:0001030405

VL - 38

SP - 2729

EP - 2738

JO - Heterocycles

JF - Heterocycles

SN - 0385-5414

IS - 12

ER -