Unusually efficient deformylative synthesis of 1,2,8,9-tetrasubstituted dipyrrins from 4,5-disubstituted pyrrole-2-carbaldehydes

Mitsunori Oda; Yurie Fujiwara; Yoshimitsu Kumai; Akira Ohta; Ryuta Miyatake

doi:10.3987/COM-14-S(K)10

Unusually efficient deformylative synthesis of 1,2,8,9-tetrasubstituted dipyrrins from 4,5-disubstituted pyrrole-2-carbaldehydes

Mitsunori Oda^*, Yurie Fujiwara, Yoshimitsu Kumai, Akira Ohta, Ryuta Miyatake

^*Corresponding author for this work

Center for Environmental Conservation and Research Safety

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

1 Scopus citations

Abstract

Upon heating in a mixture of hydrobromic acid and acetic acid, 4-arylmethyl-5-(4-methoxyphenyl)pyrrole-2-carbaldehydes (9a-c) react to give 2,8-bis(arylmethyl)-1,9-bis(4-methoxyphenyl)dipyrrins (10a-c) in high yields, demonstrating the first example of an unusually efficient deformylative transformation of pyrrole-2-carbaldehyde to dipyrrin. Dipyrrins 10 show a clear color change from red to blue, when exposed to Brønsted acid. Structure of 10a·H+ was determined by X-ray crystallographic analysis. The absorption change of 10a in the presence of a metal ion was also studied.

Original language	English
Pages (from-to)	238-251
Number of pages	14
Journal	Heterocycles
Volume	90
Issue number	1
DOIs	https://doi.org/10.3987/COM-14-S(K)10
State	Published - 2015

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

Access to Document

10.3987/COM-14-S(K)10

Cite this

@article{24c0b516db434a87a8aa911c7a003cb6,

title = "Unusually efficient deformylative synthesis of 1,2,8,9-tetrasubstituted dipyrrins from 4,5-disubstituted pyrrole-2-carbaldehydes",

abstract = "Upon heating in a mixture of hydrobromic acid and acetic acid, 4-arylmethyl-5-(4-methoxyphenyl)pyrrole-2-carbaldehydes (9a-c) react to give 2,8-bis(arylmethyl)-1,9-bis(4-methoxyphenyl)dipyrrins (10a-c) in high yields, demonstrating the first example of an unusually efficient deformylative transformation of pyrrole-2-carbaldehyde to dipyrrin. Dipyrrins 10 show a clear color change from red to blue, when exposed to Br{\o}nsted acid. Structure of 10a·H+ was determined by X-ray crystallographic analysis. The absorption change of 10a in the presence of a metal ion was also studied.",

author = "Mitsunori Oda and Yurie Fujiwara and Yoshimitsu Kumai and Akira Ohta and Ryuta Miyatake",

note = "Publisher Copyright: {\textcopyright} 2015 The Japan Institute of Heterocyclic Chemistry.",

year = "2015",

doi = "10.3987/COM-14-S(K)10",

language = "英語",

volume = "90",

pages = "238--251",

journal = "Heterocycles",

issn = "0385-5414",

publisher = "Japan Institute of Heterocyclic Chemistry",

number = "1",

}

TY - JOUR

T1 - Unusually efficient deformylative synthesis of 1,2,8,9-tetrasubstituted dipyrrins from 4,5-disubstituted pyrrole-2-carbaldehydes

AU - Oda, Mitsunori

AU - Fujiwara, Yurie

AU - Kumai, Yoshimitsu

AU - Ohta, Akira

AU - Miyatake, Ryuta

PY - 2015

Y1 - 2015

N2 - Upon heating in a mixture of hydrobromic acid and acetic acid, 4-arylmethyl-5-(4-methoxyphenyl)pyrrole-2-carbaldehydes (9a-c) react to give 2,8-bis(arylmethyl)-1,9-bis(4-methoxyphenyl)dipyrrins (10a-c) in high yields, demonstrating the first example of an unusually efficient deformylative transformation of pyrrole-2-carbaldehyde to dipyrrin. Dipyrrins 10 show a clear color change from red to blue, when exposed to Brønsted acid. Structure of 10a·H+ was determined by X-ray crystallographic analysis. The absorption change of 10a in the presence of a metal ion was also studied.

AB - Upon heating in a mixture of hydrobromic acid and acetic acid, 4-arylmethyl-5-(4-methoxyphenyl)pyrrole-2-carbaldehydes (9a-c) react to give 2,8-bis(arylmethyl)-1,9-bis(4-methoxyphenyl)dipyrrins (10a-c) in high yields, demonstrating the first example of an unusually efficient deformylative transformation of pyrrole-2-carbaldehyde to dipyrrin. Dipyrrins 10 show a clear color change from red to blue, when exposed to Brønsted acid. Structure of 10a·H+ was determined by X-ray crystallographic analysis. The absorption change of 10a in the presence of a metal ion was also studied.

UR - http://www.scopus.com/inward/record.url?scp=84923286897&partnerID=8YFLogxK

U2 - 10.3987/COM-14-S(K)10

DO - 10.3987/COM-14-S(K)10

M3 - 学術論文

AN - SCOPUS:84923286897

SN - 0385-5414

VL - 90

SP - 238

EP - 251

JO - Heterocycles

JF - Heterocycles

IS - 1

ER -

Unusually efficient deformylative synthesis of 1,2,8,9-tetrasubstituted dipyrrins from 4,5-disubstituted pyrrole-2-carbaldehydes

Abstract

ASJC Scopus subject areas

Access to Document

Fingerprint

Cite this