Synthesis in the diazasteroid group XI. A convenient route to the 4,8‐diazasteroid system | Zendy

Yamazaki Takao | Zendy; Takahata Hiroki | Zendy; Matsuura Tomoko | Zendy; Castle Raymond N. | Zendy

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Synthesis in the diazasteroid group XI. A convenient route to the 4,8‐diazasteroid system

Author(s) -

Yamazaki Takao,

Takahata Hiroki,

Matsuura Tomoko,

Castle Raymond N.

Publication year - 1979

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.5570160324

Subject(s) - chemistry , synthon , cyclopentanone , cyclohexanone , yield (engineering) , acetic anhydride , adduct , hydrolysis , acetic acid , catalysis , ring (chemistry) , organic chemistry , condensation , medicinal chemistry , materials science , physics , metallurgy , thermodynamics

The reaction of 1,6‐naphthyridine 3 with acetic anhydride results in the formation of the 1:1 adduct 4 . Upon catalytic hydrogenation followed by acid hydrolysis and esterification, 4 affords 7 as an A‐B steroid ring system synthon in moderate yield. Upon condensation with cyclopentanone and cyclohexanone, 7 , gives the 4,8‐diazasteroid system 8 and the D‐homo compound 9 , respectively.

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