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.

Tetrahedron Letters
1994.0

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 substance 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.

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