Quinoline alkaloids. Part XI. A study of the Claisen rearrangement of the 3,3-dimethylallyl ether of 4-hydroxy-1-methyl-2-quinolone. Synthesis of ifflaiamine and the identification of a new alkaloid from Flindersia ifflaiana F. Muell

Abstract

Claisen rearrangement of 1 -methyi-4-(3-methylbut-2-enyloxy)-2-quinolone resulted mainly in abnormal reaction to give a 1,2-dimethyIallylquinoline and its linear and angular cyclisation products. The intermediate 1,l -dimethylailylquinoline was trapped as its acetate which w a s cyclised to ifflaiamine with hydrobromic acid. An isomeric furanoquinoline alkaloid is shown to occur with ifflaiamine in Flindersia ifflaiana and the biogenesis of the two alkaloids is discussed.

Application of the Claisen rearrangement to the synthesis of heterocyclic bicyclo[2,2,2]octenones: an approach to the morellins based on new biogenetic suggestions

“…are lost and the most intense peak is at m / e 363 ( M - [15][16][17][18][19][20][21][22][23][24][25][26][27][28]…”

One-Step Synthesis for the Preparation of Quinoline Alkaloid Analogues

“…A simple modification that proves the generality of this method was to employ the suggested route to analogues such as 4H-pyrido[2,3-d] [3,1]oxazin-4-ones (9, X ) N) to obtain 3,3-disubstituted 1,8-naphthyridine-2,4-diones, a new class of molecules (Scheme 2, reaction A).…”

“…For the preparation of benzo-or pyrido[3,1]oxazin-4-ones, see: (a) Krantz A.; Spencer W. R.; Tam F. T. J. Med. Chem.…”

“…In the past decade, several scientific groups have managed to isolate a large number of alkaloids that belong to the quinoline class of compounds. − Isolable natural products of this class constitute two large groups of quinoline derivatives, the 3,3-disubstituted quinoline-2,4-diones ( 1 ) and the 2-substituted quinoline-4-ones ( 2 ), pertaining to the antibacterials collectively known as “quinolones” . Quinoline alkaloids of the first group have been isolated from different species of plants, such as Haplophyllum tuberculatum 3 and Esenbeckia flava .…”

“…In the past decade, several scientific groups have managed to isolate a large number of alkaloids that belong to the quinoline class of compounds. [1][2][3][4][5][6][7] Isolable natural products of this class constitute two large groups of quinoline derivatives, the 3,3-disubstituted quinoline-2,4-diones (1) and the 2-substituted quinoline-4-ones (2), pertaining to the antibacterials collectively known as "quinolones". 8 Quinoline alkaloids of the first group have been isolated from different species of plants, such as Haplophyllum tuberculatum 3 and Esenbeckia flaVa.…”