Facile Gold-Catalyzed Heterocyclization of Terminal Alkynes and Cyanamides Leading to Substituted 2-Amino-1,3-Oxazoles

被引:71
作者
Rassadin, Valentin A. [1 ]
Boyarskiy, Vadim P. [1 ]
Kukushkin, Vadim Yu [1 ]
机构
[1] St Petersburg State Univ, Inst Chem, St Petersburg 198504, Russia
关键词
EFFICIENT SYNTHESIS; OXIDATIVE CYCLIZATION; REARRANGEMENT; COMPLEXES; CARBENES; INHIBITOR; DISCOVERY; LIGANDS; CYCLOISOMERIZATION; TRANSFORMATIONS;
D O I
10.1021/acs.orglett.5b01592
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Facile gold-catalyzed heterocyclization based upon intermolecular trapping of the generated alpha-oxo gold carbenes with various cyanamides (RRNCN)-R-2-N-3 (R-2/R-3 = Alk/Alk, -(CH2)(2)O(CH2)(2)-, Ar/Ar, Ar/H) has been developed. In most cases, 2-amino-1,3-oxazoles fiinctionalized at the nitrogen atom as well as at the fifth position of the heterocyclic ring (12 examples) were isolated hi good to moderate yields.
引用
收藏
页码:3502 / 3505
页数:4
相关论文
共 72 条
[1]  
[Anonymous], COMPR COORD CHEM 2
[2]  
[Anonymous], 1981, CHEM HETEROCYC COMPO
[3]   AuBr3-catalyzed cyclization of o-(alkynyl)nitrobenzenes.: Efficient synthesis of isatogens and anthranils [J].
Asao, N ;
Sato, K ;
Yamamoto, Y .
TETRAHEDRON LETTERS, 2003, 44 (30) :5675-5677
[4]   Phosphaalkyne hydrometalation:: Synthesis and reactivity of the complexes [Ru(P=CHCMe3)Cl(CA)(PPh3)2] (A = O, S) [J].
Bedford, RB ;
Hill, AF ;
Jones, C ;
White, AJP ;
Williams, DJ ;
Wilton-Ely, JDET .
ORGANOMETALLICS, 1998, 17 (21) :4744-4753
[5]   Platinum-Catalyzed Oxoarylations of Ynamides with Nitrones [J].
Bhunia, Sabyasachi ;
Chang, Chin-Jung ;
Liu, Rai-Shung .
ORGANIC LETTERS, 2012, 14 (21) :5522-5525
[6]   Coordination chemistry of dialkylcyanamides: Binding properties, synthesis of metal complexes, and ligand reactivity [J].
Bokach, Nadezhda A. ;
Kukushkin, Vadim Yu. .
COORDINATION CHEMISTRY REVIEWS, 2013, 257 (15-16) :2293-2316
[7]   2-Anilino-4-aryl-1,3-thiazole inhibitors of valosin-containing protein (VCP or p97) [J].
Bursavich, Matthew G. ;
Parker, Daniel P. ;
Willardsen, J. Adam ;
Gao, Zhong-Hua ;
Davis, Thaylon ;
Ostanin, Kirill ;
Robinson, Rosann ;
Peterson, Ashley ;
Cimbora, Daniel M. ;
Zhu, Ju-Fen ;
Richards, Burt .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (05) :1677-1679
[8]   Phenylcyanamide ligands and their metal complexes [J].
Crutchley, RJ .
COORDINATION CHEMISTRY REVIEWS, 2001, 219 :125-155
[9]   Gold(I)-Catalyzed Intermolecular Oxyarylation of Alkynes: Unexpected Regiochemistry in the Alkylatioin of Arenes [J].
Cuenca, Ana B. ;
Montserrat, Sergi ;
Hossain, Kabir M. ;
Mancha, Gisela ;
Lledos, Agusti ;
Medio-Simon, Mercedes ;
Ujaque, Gregori ;
Asensio, Gregorio .
ORGANIC LETTERS, 2009, 11 (21) :4906-4909
[10]   Discovery of N-[2-[2-[[3-methoxy-4-(5-oxazolyl)phenyl]-amino]-5-oxazolyl]phenyl]-N-methyl-4-morpholineacetamide as a novel and potent inhibitor of inosine monophosphate dehydrogenase with excellent in vivo activity [J].
Dhar, TGM ;
Shen, ZQ ;
Guo, JQ ;
Liu, CJ ;
Watterson, SH ;
Gu, HH ;
Pitts, WJ ;
Fleener, CA ;
Rouleau, KA ;
Sherbina, NZ ;
McIntyre, KW ;
Witmer, MR ;
Tredup, JA ;
Chen, BC ;
Zhao, RL ;
Bednarz, MS ;
Cheney, DL ;
MacMaster, JF ;
Miller, LM ;
Berry, KK ;
Harper, TW ;
Barrish, JC ;
Hollenbaugh, DL ;
Iwanowicz, EJ .
JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (11) :2127-2130