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- W2346804819 endingPage "8338" @default.
- W2346804819 startingPage "8332" @default.
- W2346804819 abstract "Isonitrile 1 due to its carbene-like reactivity serves generally as a one-carbon synthon in a diverse set of organic transformations. We report in this article that the isocyano group can also act as a polarized triple bond to undergo, as a two-atom synthon, heteroannulation with primary propargylamines 15. In addition, we serendipitously discovered that the reaction pathways can be modulated by simply changing the catalyst loading. In the presence of 0.1 equiv of Yb(OTf)3 or TfOH, the reaction between 1 and 15 afforded exclusively imidazoles 16 by a formal [3+2] cycloaddition. At a higher catalyst loading (Yb(OTf)3 (0.4 equiv) or TfOH (0.5 equiv)) under otherwise identical conditions, the same reaction furnished 1,6-dihydropyrimidines 17 in good to excellent yields by way of a formal [4+2] cycloaddition process. Mechanistic investigations indicated that both annulations went through an amidine intermediate resulting from the insertion of the isocyano group to the NH bond of the primary amine. Subsequent catalyst-loading-dependent 5-exo-dig or 6-endo-dig cyclization provided selectively the two heterocycles, respectively." @default.
- W2346804819 created "2016-06-24" @default.
- W2346804819 creator A5005998007 @default.
- W2346804819 creator A5046225712 @default.
- W2346804819 creator A5055586375 @default.
- W2346804819 creator A5080389064 @default.
- W2346804819 date "2016-05-03" @default.
- W2346804819 modified "2023-09-30" @default.
- W2346804819 title "Switchable [3+2] and [4+2] Heteroannulation of Primary Propargylamines with Isonitriles to Imidazoles and 1,6-Dihydropyrimidines: Catalyst Loading Enabled Reaction Divergence" @default.
- W2346804819 cites W1268065478 @default.
- W2346804819 cites W1479861022 @default.
- W2346804819 cites W1668709012 @default.
- W2346804819 cites W1907249425 @default.
- W2346804819 cites W1940784104 @default.
- W2346804819 cites W1947481673 @default.
- W2346804819 cites W1963656888 @default.
- W2346804819 cites W1966069936 @default.
- W2346804819 cites W1974840967 @default.
- W2346804819 cites W1976531375 @default.
- W2346804819 cites W1979818452 @default.
- W2346804819 cites W1980860171 @default.
- W2346804819 cites W1980943239 @default.
- W2346804819 cites W1981921176 @default.
- W2346804819 cites W1986365713 @default.
- W2346804819 cites W1989897311 @default.
- W2346804819 cites W1990137156 @default.
- W2346804819 cites W1991844421 @default.
- W2346804819 cites W1992926232 @default.
- W2346804819 cites W1993060089 @default.
- W2346804819 cites W1996460992 @default.
- W2346804819 cites W1999147771 @default.
- W2346804819 cites W2000397973 @default.
- W2346804819 cites W2000798758 @default.
- W2346804819 cites W2003754737 @default.
- W2346804819 cites W2006112744 @default.
- W2346804819 cites W2009853675 @default.
- W2346804819 cites W2010278102 @default.
- W2346804819 cites W2012961504 @default.
- W2346804819 cites W2013273979 @default.
- W2346804819 cites W2016503001 @default.
- W2346804819 cites W2019845694 @default.
- W2346804819 cites W2021836865 @default.
- W2346804819 cites W2031125023 @default.
- W2346804819 cites W2032236822 @default.
- W2346804819 cites W2032735202 @default.
- W2346804819 cites W2033404396 @default.
- W2346804819 cites W2039625639 @default.
- W2346804819 cites W2040337349 @default.
- W2346804819 cites W2040865710 @default.
- W2346804819 cites W2049822290 @default.
- W2346804819 cites W2050496558 @default.
- W2346804819 cites W2051741129 @default.
- W2346804819 cites W2052584412 @default.
- W2346804819 cites W2053596784 @default.
- W2346804819 cites W2053698356 @default.
- W2346804819 cites W2054561630 @default.
- W2346804819 cites W2056297591 @default.
- W2346804819 cites W2056845769 @default.
- W2346804819 cites W2057636386 @default.
- W2346804819 cites W2058447513 @default.
- W2346804819 cites W2059065568 @default.
- W2346804819 cites W2062835263 @default.
- W2346804819 cites W2064077343 @default.
- W2346804819 cites W2067258370 @default.
- W2346804819 cites W2068080814 @default.
- W2346804819 cites W2068507081 @default.
- W2346804819 cites W2069279756 @default.
- W2346804819 cites W2069318333 @default.
- W2346804819 cites W2070225323 @default.
- W2346804819 cites W2070727975 @default.
- W2346804819 cites W2072449364 @default.
- W2346804819 cites W2074226317 @default.
- W2346804819 cites W2075664317 @default.
- W2346804819 cites W2076871774 @default.
- W2346804819 cites W2077074100 @default.
- W2346804819 cites W2077384121 @default.
- W2346804819 cites W2081584138 @default.
- W2346804819 cites W2083022399 @default.
- W2346804819 cites W2085893339 @default.
- W2346804819 cites W2088066153 @default.
- W2346804819 cites W2089374817 @default.
- W2346804819 cites W2090718785 @default.
- W2346804819 cites W2091259233 @default.
- W2346804819 cites W2091671954 @default.
- W2346804819 cites W2095440822 @default.
- W2346804819 cites W2096464216 @default.
- W2346804819 cites W2096888112 @default.
- W2346804819 cites W2098812000 @default.
- W2346804819 cites W2100869008 @default.
- W2346804819 cites W2101979337 @default.
- W2346804819 cites W2102907090 @default.
- W2346804819 cites W2108670661 @default.
- W2346804819 cites W2112613647 @default.
- W2346804819 cites W2114114110 @default.
- W2346804819 cites W2117994543 @default.
- W2346804819 cites W2118700728 @default.
- W2346804819 cites W2119788288 @default.
- W2346804819 cites W2122162627 @default.