Synthesis of 1-azaazulenes using ring-opening cyclization of spirocyclopropane with amine

Hisanori Nambu; Yuta Onuki; Koga Yamazaki; Takayuki Yakura

doi:10.3987/COM-20-S(K)67

Synthesis of 1-azaazulenes using ring-opening cyclization of spirocyclopropane with amine

Hisanori Nambu^*, Yuta Onuki, Koga Yamazaki, Takayuki Yakura

^*Corresponding author for this work

Synthetic and Biomolecular Organic Chemistry

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

1 Scopus citations

Abstract

Synthesis of 1-azaazulenes using ring-opening cyclization of spirocyclopropane with a primary amine was accomplished. The reaction of cycloheptane-1,3-dione-2-spirocyclopropane with 2,4-dimethoxybenzylamine in refluxing acetonitrile resulted in a 94% yield of 1,2,3,6,7,8-hexahydrocyclohepta[b]pyrrol-4(5H)-one. The obtained product was successfully converted into 1-azaazulenes by deprotecting the amino-protecting group followed by oxidation.

Original language	English
Journal	Heterocycles
Volume	103
Issue number	2
DOIs	https://doi.org/10.3987/COM-20-S(K)67
State	Published - 2021

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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title = "Synthesis of 1-azaazulenes using ring-opening cyclization of spirocyclopropane with amine",

abstract = "Synthesis of 1-azaazulenes using ring-opening cyclization of spirocyclopropane with a primary amine was accomplished. The reaction of cycloheptane-1,3-dione-2-spirocyclopropane with 2,4-dimethoxybenzylamine in refluxing acetonitrile resulted in a 94% yield of 1,2,3,6,7,8-hexahydrocyclohepta[b]pyrrol-4(5H)-one. The obtained product was successfully converted into 1-azaazulenes by deprotecting the amino-protecting group followed by oxidation.",

author = "Hisanori Nambu and Yuta Onuki and Koga Yamazaki and Takayuki Yakura",

note = "Publisher Copyright: {\textcopyright} 2021 The Japan Institute of Heterocyclic Chemistry",

year = "2021",

doi = "10.3987/COM-20-S(K)67",

language = "英語",

volume = "103",

journal = "Heterocycles",

issn = "0385-5414",

publisher = "Japan Institute of Heterocyclic Chemistry",

number = "2",

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T1 - Synthesis of 1-azaazulenes using ring-opening cyclization of spirocyclopropane with amine

AU - Nambu, Hisanori

AU - Onuki, Yuta

AU - Yamazaki, Koga

AU - Yakura, Takayuki

PY - 2021

Y1 - 2021

N2 - Synthesis of 1-azaazulenes using ring-opening cyclization of spirocyclopropane with a primary amine was accomplished. The reaction of cycloheptane-1,3-dione-2-spirocyclopropane with 2,4-dimethoxybenzylamine in refluxing acetonitrile resulted in a 94% yield of 1,2,3,6,7,8-hexahydrocyclohepta[b]pyrrol-4(5H)-one. The obtained product was successfully converted into 1-azaazulenes by deprotecting the amino-protecting group followed by oxidation.

AB - Synthesis of 1-azaazulenes using ring-opening cyclization of spirocyclopropane with a primary amine was accomplished. The reaction of cycloheptane-1,3-dione-2-spirocyclopropane with 2,4-dimethoxybenzylamine in refluxing acetonitrile resulted in a 94% yield of 1,2,3,6,7,8-hexahydrocyclohepta[b]pyrrol-4(5H)-one. The obtained product was successfully converted into 1-azaazulenes by deprotecting the amino-protecting group followed by oxidation.

UR - http://www.scopus.com/inward/record.url?scp=85108276069&partnerID=8YFLogxK

U2 - 10.3987/COM-20-S(K)67

DO - 10.3987/COM-20-S(K)67

M3 - 学術論文

AN - SCOPUS:85108276069

SN - 0385-5414

VL - 103

JO - Heterocycles

JF - Heterocycles

IS - 2

ER -

Synthesis of 1-azaazulenes using ring-opening cyclization of spirocyclopropane with amine

Abstract

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