Unexpected Behavior of Enaminones: Interesting New Routes to 1,6-Naphthyridines, 2-Oxopyrrolidines and Pyrano[4,3,2-de][1,6]naphthyridines

Molecules

Moustafa Sherief Moustafa¹  Saleh Mohammed Al-Mousawi¹  Noha Mohamed Hilmy¹  Yehia A. Ibrahim¹  Johannes C. Liermann¹  Herbert Meier¹ 

[1] ¹Department of Chemistry, Faculty of Science, University of Kuwait, P.O. Box 5969, Safat 13060, Kuwait ²Women Students-Medical Studies & Sciences Sections, Department of Chemistry, College of Science, King Saud University, Riyadh, KSA, P.O. Box 22452, Riyadh 11495, Saudi Arabia ³Johannes Gutenberg — Universität Mainz, Institute of Organic Chemistry, Mainz, Germany

关键词: enaminones;    3-amino-2-cyanopent-2-enedinitrile;    7-amino-5-oxo-5;    6-dihydro-1;    6-naphthyridine-8-carbonitrile;    2-aminoprop-1-ene-1;    1;    3-tricarbonitrile;   

DOI  :  10.3390/molecules18010276

来源: mdpi

【 摘 要 】

Reaction of enaminones 1a–d with 2-aminoprop-1-ene-1,1,3-tricarbonitrile (2) in the presence of AcOH/NH₄OAc afforded 7-amino-5-oxo-5,6-dihydro-1,6-naphthyridine-8-carbonitrile derivatives 9a–d. On the other hand, 2-aminopyrano[4,3,2-de] [1,6]naphthyridine-3-carbonitriles 20a–c,e were the only obtained products from the reactions of 1a–d with 2 in the presence of AcOH/NaOAc, while 1d afforded [3,5-bis-(4-chloro-benzoyl)-phenyl]-(4-chloro-phenyl)-methanone 21 under the same condition. The reaction of 2 with diethyl acetylenedicarboxylate in the presence of AcOH/NH₄OAc afforded (4-cyano-5-dicyanomethylene-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)-acetic acid ethyl ester 15B.

【 授权许可】

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