2019
DOI: 10.1002/chem.201903139
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Synthesis of Benzo[b]azocin‐2‐ones by Aryl Amination and Ring‐Expansion of α‐(Iodophenyl)‐β‐oxoesters

Abstract: Transformation of β‐oxoesters with PhI(OCOCF3)2 leads to α‐(ortho‐iodophenyl)‐β‐oxoesters. These materials are the starting point for the synthesis of 6‐carboxybenzo[b]azocin‐2‐ones by a sequence of aryl amination and ring transformation. This reaction sequence starts with copper‐catalyzed formation of N‐alkyl anilines from the iodoarenes and primary amines in the presence of K3PO4 as stoichiometric base. The intermediate products underwent ring transformation by addition of the nitrogen into the carbonyl grou… Show more

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Cited by 14 publications
(9 citation statements)
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References 61 publications
(39 reference statements)
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“…The synthesis of compounds A1–21 starting from intermediate 1 was accomplished as depicted in Scheme 4 . The coupling of the organic acids with amidine 1 to form the corresponding derivatives B1–21 was achieved by common coupling reagents such as N,N' -dicyclohexylcarbodiimide (DCC) or ( O -(7-aza-1 H -benzotriazol-1-yl)- N , N , N ', N '-tetramethyluronium hexafluorophosphate) (HATU) [ 33 ] in DMF or CH 2 Cl 2 with either N,N -diisopropylethylamine (DIPEA) or 4-dimethylaminopyridine (DMAP) as the base. Then, the palladium-catalyzed hydrogenation of compounds B1–21 in THF or EtOAc led to the hydroxy derivatives C1–21 .…”
Section: Resultsmentioning
confidence: 99%
“…The synthesis of compounds A1–21 starting from intermediate 1 was accomplished as depicted in Scheme 4 . The coupling of the organic acids with amidine 1 to form the corresponding derivatives B1–21 was achieved by common coupling reagents such as N,N' -dicyclohexylcarbodiimide (DCC) or ( O -(7-aza-1 H -benzotriazol-1-yl)- N , N , N ', N '-tetramethyluronium hexafluorophosphate) (HATU) [ 33 ] in DMF or CH 2 Cl 2 with either N,N -diisopropylethylamine (DIPEA) or 4-dimethylaminopyridine (DMAP) as the base. Then, the palladium-catalyzed hydrogenation of compounds B1–21 in THF or EtOAc led to the hydroxy derivatives C1–21 .…”
Section: Resultsmentioning
confidence: 99%
“…We relied on a literature procedure applying the hypervalent iodine reagent PhI(OAc) 2 . [ 25 ] First of all, the parent unsubstituted amide 21e was prepared in 93 % yield by activation of the acid 20 with Boc 2 O and conversion of the mixed anhydride with hartshorn salt. The degradation proceeded with PhI(OAc) 2 and the intermediate isocyanate was solvolyzed with MeOH to furnish the carbamate 22 , however, the yield was moderate (44 %).…”
Section: Resultsmentioning
confidence: 99%
“…Synthesis of compounds A1 ‐ A9 starting from intermediate 1 was accomplished as depicted in scheme 2. Coupling of the organic acids with amidine 1 to form the corresponding derivatives B1 ‐ B9 was achieved by coupling reagents such as N,N′ ‐dicyclohexylcarbodiimide (DCC) or ( O ‐(7‐Aza‐ 1H ‐benzotriazol‐1‐yl)‐ N,N,N′,N′ ‐tetramethyluronium hexafluorophosphate) (HATU), [19] in CH 2 Cl 2 or N,N ‐dimethylformamide (DMF) whereas N,N ‐diisopropylethylamine (DIPEA) or 4‐dimethylaminopyridine (DMAP) were used as base. Palladium catalyzed hydrogenation of compounds B1 ‐ B9 in tertrahydrofuran (THF) or EtOAc led to afford hydroxy derivatives C1 ‐ C9 .…”
Section: Figurementioning
confidence: 99%