Synthesis in the diazasteroid group VI.  A synthesis of 2,3‐dimethoxy‐15‐methyl‐8,15‐diazaestra‐1,3,5(10)triene | Zendy

Yamazaki Takao | Zendy; Nagata Masanori | Zendy; Matoba Katsuhide | Zendy; Takahata Hiroki | Zendy; Castle Raymond N. | Zendy

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Synthesis in the diazasteroid group VI. A synthesis of 2,3‐dimethoxy‐15‐methyl‐8,15‐diazaestra‐1,3,5(10)triene

Author(s) -

Yamazaki Takao,

Nagata Masanori,

Matoba Katsuhide,

Takahata Hiroki,

Castle Raymond N.

Publication year - 1977

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570140323

Subject(s) - chemistry , quinolizidine , amide , ring (chemistry) , derivative (finance) , stereochemistry , group (periodic table) , medicinal chemistry , organic chemistry , alkaloid , financial economics , economics

Homoveratrylamine (II) was condensed with 3‐(2‐carbomethoxyethyl)‐1,3‐dimethyl‐2‐pyrrol‐idone (Ib) to furnish the corresponding amide (III), which was subjected to the Bischler‐Napieralski reaction to afford the corresponding dihydroisoquinoline derivative (IV). Compound V was obtained by the reductive ring closure of Vila which was obtained by the hydrogena‐tion of IV. The stereochemistry of V is proposed to have the anti‐trans‐trans quinolizidine conformation.

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