Chemical studies on 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one in connection with 6-methoxy-2-benzoxazolinone, an auxin-inhibiting substance of Zea mays L.

Seiji Kosemura, Shosuke Yamamura, Toyoaki Anai, Koji Hasegawa

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Some chemical studies on 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (DIMBOA, 1) and related compounds from Zea mays L. have been carried out, where DIMBOA (1) has been very rapidly converted into 6-methoxy-2-benzoxazolinone (MBOA, 2), an auxin-inhibiting substanse of maize, in the presence of acetic anhydride at room temperature. Therefore, such an enzymatic acylation of N-OH group of DIMBOA (1) as in vitro presumably plays an important role on phototropism.

Original languageEnglish
Pages (from-to)8221-8224
Number of pages4
JournalTetrahedron Letters
Volume35
Issue number44
DOIs
Publication statusPublished - 1994 Oct 31

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Indoleacetic Acids
Zea mays
Phototropism
Acylation
Temperature
2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one
6-methoxybenzoxazolinone

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Chemical studies on 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one in connection with 6-methoxy-2-benzoxazolinone, an auxin-inhibiting substance of Zea mays L. / Kosemura, Seiji; Yamamura, Shosuke; Anai, Toyoaki; Hasegawa, Koji.

In: Tetrahedron Letters, Vol. 35, No. 44, 31.10.1994, p. 8221-8224.

Research output: Contribution to journalArticle

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