1124
Jing YF, et al. Sci China Chem August (2014) Vol.57 No.8
15: 235–241
might provide an impetus for exploring the versatility and
special qualities of lanthanide-catalyzed annulation reac-
tions. This methodology is also suitable for the synthesis of
various benzannulated 1,3-diheteroatom cyclic thioketones
from readily available 1,2-disubstituted benzenes. Com-
pared with other methods using similar substrates, the ad-
vantages of the present methodology include easy access to
the reagents, simple operation, and high chemoselectivity,
without the need for gaseous carbon monoxide and addi-
tives.
13 a) Saouma CT, Kaminsky W, Mayer JM. Protonation and concerted
proton-electron transfer reactivity of a bis-benzimidazolate ligated
[2Fe-2S] model for Rieske clusters. J Am Chem Soc, 2012, 134:
7293–9296; b) Dolores Santana M, Garcia-Bueno, R, Garcia G.
Benzazolate complexes of pentacoordinate nickel(II). Synthesis,
spectroscopic study and luminescent response towards metal cations.
Polyhedron, 2013, 61: 161–171
14 Cacchi S, Fabrizi G. Update 1 of: synthesis and functionalization of
indoles through palladium-catalyzed reactions. Chem Rev, 2011, 111:
215–283
15 Porzelle A, Woodrow MD, Tomkinson NCO. Synthesis of benzoxa-
zolones from nitroarenes or aryl halides. Org Lett, 2010, 12: 812–815
16 Barbero N, Carril M, SanMartin R, Domínguez E. Copper-catalyzed
intramolecular N-arylation of ureas in water: a novel entry to benzo-
imidazolones. Tetrahedron, 2008, 64: 7283–7288
17 Li JJ, Zhang YH, Jiang YW, Ma DW. CuI-catalyzed one-pot synthe-
sis of benzothiazolones from 2-iodoanilines-derived carbamates and
sodium sulfide. Tetrahedron Lett, 2012, 53: 2511–2513
18 Li ZG, Huang H, Sun HB, Jiang HL, Liu HJ. Microwave-assisted ef-
ficient and convenient synthesis of 2,4(1H,3H)-quinazolinediones
and 2-thioxoquinazolines. Comb Chem, 2008, 10: 484–486
19 Patonay T, Hegedus L, Mogyorodi F, Zolnai L. α-Haloalkyl halofor-
mates and related compounds. 2. Synthesis of dichloromethyl car-
bonates and their transformation to carbamates. Synth Commun, 1994,
24: 2507–2513
20 Schwiebert KE, Chin DN, MacDonald JC, Whitesides GM. Engi-
neering the solid state with 2-benzimidazolones. J Am Chem Soc,
1996, 118: 4018–4029
21 Yue F, Toshihide B, Yoshio O. Carbonylation of o-phenylenediamine
and o-aminophenol with dimethyl carbonate using lead compounds as
catalysts. J Catal, 2001, 197: 91–97
22 Singh MS, Singh P, Singh S. Synthesis of benzoxazol-2-ones, ben-
zothiazol-2-ones and their 2-thione analogs: efficient conversion of
2-thione to 2-oxo analogs. Indian J Chem, 2007, 46: 1666–1671
23 Senthilkumar UP, Arumugam N, Pandian PS, Ganesan MS. Process
for the preparation of a β-lactam intermediate. Indian Patent,
2006CH01837, 2008-11-28
This work was supported by the National Natural Science Foundation of
China (21132002, 21272038) and the National Basic Research Program of
China (2011CB825300).
1
Busacca CA, Fandrick DR, Song JJ, Senanayaka CH. The growing
impact of catalysis in the pharmaceutical industry. Adv Synth Catal,
2011, 353: 1825–1864
2
3
Wu XF, Neumann H, Beller M. Synthesis of heterocycles via
palladium-catalyzed carbonylations. Chem Rev, 2013, 113: 1–35
Kondo T, Nomura M, Ura Y, Wada K, Mitsudo T. Ruthenium-
catalyzed [2+2+1] cocyclization of isocyanates, alkynes, and CO
enables the rapid synthesis of polysubstituted maleimides. J Am
Chem Soc, 2006, 128: 14816–14817
4
5
Lv YD, Kefalidis CE, Zhou JL, Laurent M, Leng XB, Chen YF.
Versatile reactivity of a four-coordinate scandium phosphinidene
complex: reduction, addition, and CO activation reactions. J Am
Chem Soc, 2013, 135: 14784–14796
Liu WG, Lau F, Liu K, Wood HB, Zhou GC, Chen YL, Li Y, Aki-
yama TE, Castriota G, Einstein M, Wang CL, McCann ME, Doebber
TW, Wu M, Chang CH, McNamara L, McKeever B, Mosley RT,
Berger JP, Meinke PT. Benzimidazolones: a new class of selective
peroxisome proliferator-activated receptor γ (PPARγ) modulators. J
Med Chem, 2011, 54: 8541–8554
6
a) Conney AH, Burns JJJ. Physiological disposition and metabolic
fate of chlorzoxazone (paraflex) in man. Pharmacol Exp Ther, 1960,
128: 340–343; b) Poupaert J, Carato P, Colacino E, Yous S. 2(3H)-
benzoxazolone and bioisosters as “privileged scaffold” in the design
of pharmacological probes. Curr Med Chem, 2005, 12: 877–885
Wei H, Yang GF. Microwave-assisted, one-pot syntheses and fungi-
cidal activity of polyfluorinated 2-benzylthiobenzothiazoles. Bioorg
Med Chem, 2006, 14: 8280–8285
Alig L, Alsenz J, Jelkovic M, Bendels S, Benardeau A, Bleicher K,
Bourson A, David PP, Guba W, Hildbrand S, Kube D, Lubbers T,
Mayweg AV, Narquizian R, Neidhart W, Nettekoven M, Plancher
JM, Rocha C, Rogers EM, Rover S, Schneider G, Taylor S,
Waldmeier P. Benzodioxoles: novel cannabinoid-1 receptor inverse
agonists for the treatment of obesity. J Med Chem, 2008, 51: 2115–
2127
24 Takeda K, Ogura H. Studies on heterocyclic compounds. XLIII. In-
sertion reaction of carbonyl group using disuccinimido carbonate
(DSC). Synth Commun, 1982, 12: 213–217
25 Yu B, Zhang HY, Zhao YF, Chen S, Xu JL, Hao LD, Liu ZM.
DBU-based ionic-liquid-catalyzed carbonylation of o-phenylenedia-
mines with Co2 to 2-benzimidazolones under solvent-free conditions.
ACS Catal, 2013, 3: 2076–2082
26 Gabriele B, Mancuso R, Salerno G, Costa M. An improved procedure
for the palladium-catalyzed oxidative carbonylation of beta-amino
alcohols to oxazolidin-2-ones. J Org Chem, 2003, 68: 601–604
27 Sonoda N, Yamamoto G, Nakatsuka K, Kondo K, Murai S. New
synthesis of heterocycles by the reaction of amino alcohols or amino
thiols with carbon monoxide in the presence of selenium. Tetrahe-
dron Lett, 1975, 16: 1969–1972
7
8
28 Zhang J, Ma LP, Cai RF, Weng LH, Zhou XG. Substituent effects on
isocyanate insertion into a lanthanide-sulfur bond. Unexpected
construction of a coordinated thiazolate ring. Organometallics, 2005,
24: 738–742
29 Hong LC, Lin WJ, Zhang FJ, Liu RT, Zhou XG. Ln[N(SiMe3)2]3-
catalyzed cycloaddition of terminal alkynes to azides leading to
1,5-disubstituted 1,2,3-triazoles: new mechanistic features. Chem
Commun, 2013, 49: 5589–5591
9
Rzasa RM, Kaller MR, Liu G, Magal E, Nguyen TT, Osslund TD,
Powers D, Vincent J, Viswanadhan N, Wang HL, Xiong XL, Zhong
WG, Norman MH. Structure-activity relationships of 3,4-dihydro-
1H-quinazolin-2-one derivatives as potential CDK5 inhibitors.
Bioorg Med Chem, 2007, 15: 6574–6595
10 Dreyer DL, Brenner RC. Chemotaxonomy of the rutaceae. Part XIII.
Alkaloids of some Mexican zanthoxylum species. Phytochemistry,
1980, 19: 935–939
11 Nawrat CC, Moody CJ. Total synthesis of mevashuntin. Org Lett,
2012, 14: 1484–1487
12 Alagarsamy V, Solomon VR, Dhanabal K. Synthesis and pharmaco-
logical evaluation of some 3-phenyl-2-substituted-3H-quinazolin-4-
one as analgesic, anti-inflammatory agents. Bioorg Med Chem, 2007,
30 Roesky HW, Panday KK, Krebs Bernt D, Mechtild MAP, Miller MJ.
Divalent lanthanide chemistry. Preparation and crystal structures of
sodium tris[bis(trimethylsilyl)amido]europate(II) and sodium tris[bis-
(trimethylsilyl)amido]ytterbate(II), NaM[N(SiMe3)2]3. Inorg Chem,
1984, 23: 2271–2276