38186-81-1Relevant articles and documents
Metal-free decarboxylative Hetero-Diels-Alder synthesis of 3-hydroxypyridines: A rapid access to N-fused bicyclic hydroxypiperidine scaffolds
Jouanno, Laurie-Anne,Di Mascio, Vincent,Tognetti, Vincent,Joubert, Laurent,Sabot, Cyrille,Renard, Pierre-Yves
, p. 1303 - 1319 (2014/03/21)
A complete experimental and theoretical study of the thermally controlled metal-free decarboxylative hetero-Diels-Alder (HDA) reaction of 5-alkoxyoxazoles with acrylic acid is reported. This strategy offers a new entry to valuable 2,6-difunctionalized 3-hydroxypyridines from readily available 2- and 4-disubstituted 5-alkoxyoxazoles. The reaction conditions proved compatible with, among others, ketone, amide, ester, ether, and nitrile groups. The broad functional group tolerance of the protocol allows a rapid and versatile access to both hydroxyindolizidine and hydroxyquinolizidine derivatives via a pyridine dearomatization strategy.
N-ARYL-SUBSTITUTED CYCLIC AMINE DERIVATIVE AND MEDICINE CONTAINING THE SAME AS ACTIVE INGREDIENT
-
Page 38; 30, (2010/02/05)
The present invention provides an excellent squalene synthase inhibitor. Specifically, it provides a compound (I) represented by the following formula, a salt thereof or a hydrate of them. Wherein R1 represents an optionally substituted vinyl group or an aromatic ring which may be substituted; ???n is an integer of 0 to 2; ???X, Y and Z are the same as or different from each other and each represents an optionally substituted carbon atom, or an optionally substituted nitrogen a tom, sulfuratomoroxygenatom, and Y optionally represents a single bond, and when Y represents the single bond, the ring to which X, Y and Z belong is a 5-membered ring; ???CyA represents a 5- to 14 membered non-aromatic cyclic amino groupornon-aromatic cyclic amidogroupwhichmaybe substituted, and the non-aromatic cyclic amino group or the non-aromatic cyclic amido group optionally having an oxygen atom or a sulfur atom; ???W represents a chain expressed by(1) optionally substituted -CH2-CH2-,(2) optionally substituted -CH=CH-,(3) -C≡C-,(4) an optionally substituted phenylene group,(5) a single bond,(6) -NH-CO-,(7) -CO-NH-,(8) -NH-CH2-,(9) -CH2-NH-,(10) -CH2-CO-,(11) -CO-CH2-,(12) -O-(CH2)m-,(13) -(CH2)m-O- (where m represents an integer of 0 to 5),(14) -O-CH2-CR2=,(15) -O-CH2-CHR2- (where R2 represents a hydrogen atom, a C1-6 alkyl group or a halogen atom),(16) -NH-S(O)1-,(17) -S(O)1-NH-,(18) CH2-S(O)1-, or(19) -S(O)2-CH2- (where 1 represents 0, 1, or 2); and ???A represents a group having any of the following structural formulae: (wherein R3 and R4 represent independently a hydrogen atom or an optionally substituted C1-6 alkyl group, or combine through a carbon chain optionally containing a heteroatom to form a ring; ???R5 and R6 represent independently a hydrogen atom or an optionally substituted C1-6 alkyl group, or combine through a carbon chain optionally containing a heteroatom to form a ring; ???R7 represents a hydrogen atom, an optionally substituted C1-6 alkyl group, a hydroxyl group, an alkoxy group, a halogen atom or an optionally substituted amino group; ???R8 represents a hydrogen atom, a hydroxyl group, an alkoxy group, a halogen atom or an optionally substituted amino group; ???B1 represents an optionally substituted carbon atom, or an optionallysubstitutednitrogenatom, oxygen atom or sulfur atom; ???B2 represents an optionally substituted carbon atom or nitrogen atom; ???a and b represent an integer of 0 to 4, provided that a+b is an integer of 0 to 4; ???c represents 0 or 1; and----- represents a single bond or a double bond, provided that when c is 1 in which A is a quinuclidine having R8 represented by the case where R8 is a hydrogen atom or a hydroxyl group; Arl is an aromatic heterocycle; and W is one of (1) to (3), (6) to (11) and (16) to (19) are excluded).
