Isocyanate acting as a carbonyl precursor

Pyridyl group-assisted formation of 4H-pyrido[1,2-a]pyrimidin-4-ones from ketimines and isocyanates

Yoichiro Kuninobu, Shuhei Nishimura, Kazuhiko Takai

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

By the reactions of ketimines bearing a pyridyl or a picolyl group on a nitrogen atom of the imine moiety with tosylisocyanate, 4H-pyrido[1,2-a] pyrimidin-4-one derivatives could be obtained in quantitative yields. In these reactions, tosylisocyanate acts as a carbonyl precursor. The pyridyl or picolyl group is a key functional group because it is not only the constituent structure of the 4H-pyrido[1,2-a]pyrimidin-4-one framework but also the promoter of the formation of a ketene intermediate.

Original languageEnglish
Pages (from-to)203-205
Number of pages3
JournalOrganic and Biomolecular Chemistry
Volume4
Issue number2
DOIs
Publication statusPublished - Apr 14 2006
Externally publishedYes

Fingerprint

Bearings (structural)
Isocyanates
isocyanates
Imines
Functional groups
Nitrogen
Derivatives
Atoms
nitrogen atoms
imines
ketene
ketimine

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Isocyanate acting as a carbonyl precursor : Pyridyl group-assisted formation of 4H-pyrido[1,2-a]pyrimidin-4-ones from ketimines and isocyanates. / Kuninobu, Yoichiro; Nishimura, Shuhei; Takai, Kazuhiko.

In: Organic and Biomolecular Chemistry, Vol. 4, No. 2, 14.04.2006, p. 203-205.

Research output: Contribution to journalArticle

@article{293c9461ea1d4aa6a69bb973ec5bb192,
title = "Isocyanate acting as a carbonyl precursor: Pyridyl group-assisted formation of 4H-pyrido[1,2-a]pyrimidin-4-ones from ketimines and isocyanates",
abstract = "By the reactions of ketimines bearing a pyridyl or a picolyl group on a nitrogen atom of the imine moiety with tosylisocyanate, 4H-pyrido[1,2-a] pyrimidin-4-one derivatives could be obtained in quantitative yields. In these reactions, tosylisocyanate acts as a carbonyl precursor. The pyridyl or picolyl group is a key functional group because it is not only the constituent structure of the 4H-pyrido[1,2-a]pyrimidin-4-one framework but also the promoter of the formation of a ketene intermediate.",
author = "Yoichiro Kuninobu and Shuhei Nishimura and Kazuhiko Takai",
year = "2006",
month = "4",
day = "14",
doi = "10.1039/b516916j",
language = "English",
volume = "4",
pages = "203--205",
journal = "Organic and Biomolecular Chemistry",
issn = "1477-0520",
publisher = "Royal Society of Chemistry",
number = "2",

}

TY - JOUR

T1 - Isocyanate acting as a carbonyl precursor

T2 - Pyridyl group-assisted formation of 4H-pyrido[1,2-a]pyrimidin-4-ones from ketimines and isocyanates

AU - Kuninobu, Yoichiro

AU - Nishimura, Shuhei

AU - Takai, Kazuhiko

PY - 2006/4/14

Y1 - 2006/4/14

N2 - By the reactions of ketimines bearing a pyridyl or a picolyl group on a nitrogen atom of the imine moiety with tosylisocyanate, 4H-pyrido[1,2-a] pyrimidin-4-one derivatives could be obtained in quantitative yields. In these reactions, tosylisocyanate acts as a carbonyl precursor. The pyridyl or picolyl group is a key functional group because it is not only the constituent structure of the 4H-pyrido[1,2-a]pyrimidin-4-one framework but also the promoter of the formation of a ketene intermediate.

AB - By the reactions of ketimines bearing a pyridyl or a picolyl group on a nitrogen atom of the imine moiety with tosylisocyanate, 4H-pyrido[1,2-a] pyrimidin-4-one derivatives could be obtained in quantitative yields. In these reactions, tosylisocyanate acts as a carbonyl precursor. The pyridyl or picolyl group is a key functional group because it is not only the constituent structure of the 4H-pyrido[1,2-a]pyrimidin-4-one framework but also the promoter of the formation of a ketene intermediate.

UR - http://www.scopus.com/inward/record.url?scp=33645674909&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33645674909&partnerID=8YFLogxK

U2 - 10.1039/b516916j

DO - 10.1039/b516916j

M3 - Article

VL - 4

SP - 203

EP - 205

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 2

ER -