4664-27-1Relevant articles and documents
NOVEL MORPHOLINE DERIVATIVE OR SALT THEREOF
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Paragraph 0958-0962, (2016/07/05)
There is provided a morpholine derivative represented by General Formula [1A] or a salt thereof. (In the formula, a ring A represents a ring represented by General Formula [I]; * represents a bonding position; Z2 represents CH or the like; Z1 represents CR6 or the like; R6 represents a hydrogen atom or the like; X1 represents CHR7 or the like; R7 represents a hydrogen atom or the like; X2 represents CH2 or the like; R1 and R2 are the same as or different from each other, and each of R1 and R2 represents a hydrogen atom or the like; R3, R4, and R5 are the same as or different from each other, and each of R3, R4, and R5 represents a hydrogen atom, NRaRb, or the like; and each of Ra and Rb represents a hydrogen atom, a C1-8 alkyl group which may have a substituent, or the like.)
The synthesis of Nauclea indole-pyridine alkaloids. 3,4-Disubstituted and 3,4,5-trisubstituted pyridines as synthetic intermediates; a total synthesis of (+/-)-decarbomethoxy-3α- and -3β-nauclechine
Shariff, Azim,McLean, Stewart
, p. 2813 - 2820 (2007/10/02)
Synthetic routes to a number of 3,4-disubstituted and 3,4,5-trisubstituted pyridines have been explored.These pyridines, designed to be used in the synthesis of Nauclea indole-pyridine alkaloids, are potentially useful intermediates in a number of syntheses.Particular attention has been paid to more highly substituted derivatives of 4-pyridineacetic acid, and the experimental limitations associated with their synthesis and use in subsequent reactions such as the Bischler-Napieralski cyclization have been described and explained.A synthesis of decarbomethoxynauclechine from 4-methylnicotinaldehyde avoiding these difficulties was then de signed and executed.Both diastereoisomers, (+/-)-decarbomethoxy-3α-nauclechine and (+/-)-decarbomethoxy-3β-nauclechine, were obtained; the structure and stereochemistry of each was rigorously established, but it was not possible to demonstrate which corresponded to the natural alkaloid, decarbomethoxynauclechine, reported previously.