A Convenient Approach to CF3‐Containing N‐Heterocycles Based on 2‐Methoxy‐2‐methyl‐5‐(trifluoromethyl)furan‐3(2H)‐one. Issue 23 (2nd July 2015)

• Record Type: Journal Article
• Authors: Bazhin, Denis N.; Kudyakova, Yulia S.; Röschenthaler, Gerd‐Volker; Burgart, Yanina V.; Slepukhin, Pavel A.; Isenov, Maksim L.; Saloutin, Victor I.; Charushin, Valery N.
• Is Part Of: European journal of organic chemistry. Issue 23(2015)
• Page Start: 5236
• Page End: 5245
• Publication Date: 2015-07-02
• Subjects: Nitrogen heterocycles -- Oxygen heterocycles -- Fluorine -- Transimination -- Cyclization; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500737
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: New synthetic routes to trifluoromethylated N‐heterocycles based on condensations of 2‐methoxy‐2‐methyl‐5‐(trifluoromethyl)furan‐3(2 H )‐one with bifunctional N‐nucleophiles are described. For the first time, trifluoromethyl‐containing pyrazoles, pyrazolines and isoxazolines bearing hydrazone or oxime groups could be obtained by a one‐pot strategy based on reactions of 5‐(trifluoromethyl)furan‐3(2 H )‐one with two equivalents of the corresponding hydrazines or hydroxylamine in the presence of an acid. The interaction of furan‐3(2 H )‐one with ureas proceeded under mild conditions to furnish 1 H ‐furo[2, 3‐ d ]imidazol‐2(3 H )‐one derivatives in good yield. Further, a trifluoromethyl‐containing quinoxaline derivative was obtained by condensation of furan‐3(2 H )‐one with ortho ‐phenylenediamine. Abstract : Reactions of the 2‐methoxy‐2‐methyl‐5‐(trifluoromethyl)furan‐3(2 H )‐one with N‐binucleophiles are useful for the convenient preparation of trifluoromethyl‐containing pyrazoles, pyrazolines, quinoxalines, isoxazoles, 1 H ‐furo[2, 3‐ d ]imidazol‐2(3 H )‐ones.