4-Aminocarbonyl-5-hydroxy

Aus Amino-malonsaure-diamid und Formamidin-Hydroacetat272 oder Triethoxy-methan273 wird analog 4-Aminocarbonyl-5-hydroxy-imidazol (R2 = CO-NH2 79%) erhalten. 

JO-(3-Dimethylamino-propyloxy)-IOH-(dibenzo-1,4-oxaphosphorin)-10-oxid595 (90%) Dialkylphosphinsaure-(2-amino-3-chlor-3-cyan-allylester)586 Diarylphosphinsdure-(aminocarbonyl-hydroxy-methylt ster)im... 

Chemical Name N-[7 [[3-0-(aminocarbonyl)-5,5 di-C-methyl-4-0-methyl-a-L-lyxo-pyranosylj oxyj -4-hydroxy-8-methyl-2-oxo-2H-1 -benzopyran-3-yl] -4-hydroxy-3-(3-methyl-2-butenyl)benzamide... 

A highly diastereoselective alkenoylation of protected optically active a-hydroxy- and a-aminoalkanals is achieved with (alkyl-substituted) [1-(diisopropylaminocarbonyloxy)-l-[(4-tnethylphenyl)sulfonyl]-2-alkeuyl]lithium,1 ,2, generated by deprotonation with butyllithi-um in THF. During the reaction, the aminocarbonyl residue migrates and 4-methylbenzenesul-finate is eliminated. 

Wahrend 6-Hydroxy-9H-allopurin in 1 n Essigsaure zum 6-Oxo-l, 2,3,6-tetrahydro-9H-allopurin (80% d.Th. F 210°) reduziert werden kann, werden in 2n Schwefelsaure 6-Oxo-perhydro-allopurin neben 3-Amino-4-aminocarbonyl-2,3-dihydro-pyrazol (an Quecksilber beide Produkte isolierbar) erhalten1,s a-2 ... 

Bei —0,15 bis -0,4 V entsteht 3-Hydroxy-(naphtho-[ ,2-c]-oxazol) bzw. I-Hydr-oxy- (naphtho-[2,l-c]-l,2-oxazol) aus l-Nitro-2-aminocarbonyl- bzw. 2-Nitro-l-amino-carbonyl-naphthalin5 ... 

Analog reagieren 3-Nitro-2-aminocarbonyl- und 8-Nitro-l-aminocarbonyl (bzw. carboxy)-naphthalin5 zum 1 -Hydroxy-(naphtho-[2,3-c -1,2-oxazol) bzw. 8-Amino-naphthalin-1 -carbonsaure-lactam ... 

N-Diphenylmethylen- 374 N-Diphenylmethylen-O-aminocarbonyl- 612 N-[l,3-Diphenyl-propyl-(2) - 374 N-[l,3-Diphenyl-propyliden-(2)]- 374, 377, 380 N-(4-Halogen-phenyI)- 683 N-Heptyl- 375 N-Heptyl-N-acetyl- 376 N-Heptyliden- 375 N-Hcptyliden-O-acetyl- 376 0-(2-Hydroxy-athyl)-N-athoxycarbonyl- 133 N-(4-Hydroxy-phenyl)- 683 0-(2-Hydroxy-l-phenyl-athyI)-N-athoxycarbonyI-aus 0-(ci-AthoxycarbonyI-benzyl)-N-athoxycar-bonyl-hydroxylamin und Lithiumalanat 133 N-Isopropyl- 682 N-Isopropylidcn- 613 N-Methyl- 133, 682 O-Methyl-N-bcnzyliden- 377 O-Methyl-N-benzyliden- 375 0-Methyl-N-(4-chlor-benzyl)- 375 0-Methyl-N-(4-chlor-benzyliden)- 375 N-Methy -N,0-diacetyI- 682 N-(4-Methyl-phenyl)- 683 0-McthyI-N-( 1 -phenyl-athyliden)- 375 N-(4-Methylthio-phenyl)- 684 N-(4-Nitro-benzyl)- 374 N-[4-Nitro-benzyliden - 374, 377 N-(2-Nitro-phenyl)- 562 N-(4-Nitro-phenyl)- 682 N-Nitroso-N-cyclohexyl- 697 N-Octyl- 374 N-Octyl-(2)-N-acetyl- 376 N-Octyliden- 374 N-0ctyliden-(2)-0-acctyl- 376 N-(Pentafluor-phenyl)-0,N-diacetyl- 697 N-Phenyl- 474, 481, 682, 783 N-Phenylacetyl-O-benzoyl- 265 N-(l-Phenyl-athyl)- 374 N-(l-Phenyl-athyl)-N-acetyl- 376 N-(l-Phenyl-athyliden)-374, 613 N-( l-Phenyl-athyliden)-0-acetyl- 376 N-[ 1 -Phenyl-buten-( 1 )-yl-(3)-iden]- 582 N-f4-Phenyl-butyl-(2)-iden]- 581 N-Phcnyl-N,0-diacetyl- 682 N-(4-Phenylthio-phenyl)- 684 N-Propyl-N-cyclohexyl- 376 N-Propyl-N-isopropyl- 376 O-Sulfonyl- 481 N-(4-Sulfonyl-phenyI)- 683 N-(2-Vinyl-phenyl)- 698... 

Ainino t-(methylamino-hydroxy-methyl)- 597 1-Anilinocarbonyl- 136 l-Benzyl-2-aminocarbonyl- 600... 

CN stereoisomer of 3,6-diamino-Al-[6-[[(aminocarbonyl)amino]methylene]-3-(2-amino-l,4,5,6-tetrahydro-6-hydroxy-4-pyrimidinyl)-9, 12-bis(hydroxymethyl)-2,5,8,11,14-pentaoxo-1,4,7,10,13-pentaazacyclohexadec-15-y l]hexanamide... 

For a general, simple high yield indole synthesis from anilines and methylthioacetaldehyde etc. see JACS 95,588,591,2718,6508 (1973). For indoles from N-( /3 -hydroxy-ethyl aniline esters see BSC 2485(1973). For a 2-acyl-indoles in one step from orthoamino-ketones and alpha-haloketones or 2-carboxyindoles from sulfonamides of ortho-aminocarbonyls see JOC 38,3622-24(1972). Indole and 5-Br-indole in 4 steps from beta-naphthol see Chem. Het. Cpds. (Russ.) 753(1973). Indole-JOC 37,3622(1972). 

Abstract Development in the field of transition metal-catalyzed carbonylation of epoxides is reviewed. The reaction is an efficient method to synthesize a wide range of / -hydroxy carbonyl compounds such as small synthetic synthons and polymeric materials. The reaction modes featured in this chapter are ring-expansion carbonylation, alternating copolymerization, formylation, alkoxycarbonylation, and aminocarbonylation. 

Bleomycin Bleomycin is a stereoisomer of 6-amino-A-[[2-[[4-[[l-[[[2-[4-(aminocar-bonyl)[2,4i-bintiazol]-2i-yl]ethyl]amino]carbonyl]-2-hydroxypropylamino-2-hydroxy-l,3-dimethyl-4-oxobutyl]amino-l-[[2-0-[3-0-(aminocarbonyl)-a-D-... 

Phosgen266 bzw. Ammoniumhydrogencarbonat267 als Cl-Baustein liefern 4,5-Dicyan-2-hydr-oxy)- bzw. 5(4j-Aminocarbonyl-4(5)-cyan-2-hydroxy-imidazole die beide in der tautome-ren Form als 2-Oxo-2,3-dihydro-imidazole vorliegen. 

Gute Ausbeuten von 2-Hydroxy-1,3,4-oxadiazolen erreicht man auch durch Erhitzen von Kohlensaure-(2-acyl-hydrazid)-amiden oder 3-Acyl-l-aminocarbonyl-harnstoffen in Xylol424 oder Biphenyl422 ... 

Die durch Cyclisierungen von 2-Aminocarbonyl-hydrazonen mit Natronlauge zuganglichen 5-Aryl(Hetaryl)-5-hydroxy-4-methyl-3-oxo-2,3,4,5-tetrahydro-l,2,4-triazine lagem sich mit Brom/Natriumacetat in 5-Aroyl(Hetaroyl)-2-methylamino-l, 3,4-oxadiazole um560. 

Die aus Hydroximino-malonsaure-amid-nitriloxid (in situ durch Thermolyse eines Furoxans in Xylol/DMF hergeslelll)164 mil Olefinen zuganglichen 3-(Aminocarbonyl-hydrOximino-mc-thyl)-4,5-dihydro-l,2-oxazole lagern sich bei den Reaktionstemperaturen zu 4-Aminocarbo-nyl-3-(2-hydroxy-alkyl)-furazanen urn164, lft5 ... 

Acetoxy-2,4-dioxo-5-fluoro- ElOa, 288 (En f Ac-OF) 5-Aminocarbonyl-2,4-dioxo-5-fluoro-6-hydroxy- ElOb,. 355 (En + Fj/H20)... 

Few examples of stereoselectivity in 6-exo cyclizations to piperidine derivatives have been reported. The aminocarbonylation reactions of systems with an allylic hydroxy substituent that are quite stereoselective in cyclization to pyrrolidine systems (equation 106) are nonselective in cyclizations to piperidine systems.237 Cyclizations with mercury(II) acetate also proceed with low selectivity (59-69% cis isomer).237 A series of aminoalditols have been synthesized by aminomercuration of oxygen-substituted 6-(/V-benzylamino)hexenes. The stereochemistry of these cyclizations (equation 112)247 does not appear... 

As stated above, aliphatic amines are potent ligands for electrophilic transition metals and are efficient catalyst poisons in attempted alkene animation reactions. However, tosylation of the basic amino group greatly reduces its complexing ability, yet does not compromise its ability to nucleophilically attack complexed alkenes. Thus, a variety of alkenic tosamides efficiently cyclized under palladium(II) catalysis producing N-tosylenamines in excellent yield (equations 17 and 18).32 Again, this alkene amination proceeded through an unstable a-alkylpalladium(II) species, which could be intercepted by carbon monoxide, to result in an overall aminocarbonylation of alkenes. With ureas of 3-hydroxy-4-pentenyl-amines (Scheme 7), this palladium-catalyzed process was quite efficient but it was somewhat less so with... 

A 3-amino-/V-[2-chloro-4 [(3-hydroxyphenyl)methyl]aminocarbonyl benzoyl-L-alanine substituted Wang resin was /V-acylated with 2-methoxy-11-oxo-l l/7-pyrido[2,l-Z>]-quinazoline-8-carboxylic acid in A-methylpyrro-lidone in the presence of l-hydroxy-7-azabenzotriazole and diisopropylcar-bodiimide (00MIP2). The product was cleaved from the resin by treatment with 50% TFA in a mixture of CH2C12 and MeOH. 

Aminocarbonyl-ethyl)-dibenzyl- XII/1, 154 (Aminocarbonyl-methyl)-di-tert.-butyl- E2, 22 (l-Amino-ethyl)-hydroxy- E2, 309 (4-Amino-phenyl)-diphcnyl- XII/1, 149 [l-(4-Amino-phenyl)-vinyl]-hydroxy- El, 272 (3-Amino propyloxy) hydroxy El, 319 /<-Anilino benzyl) hvdmxy... 

Based upon the oxidative aminocarbonylation of terminal alkynes [141], a conjugate addition of the amine to the ynoylamide leads to the stereoselective formation of an -configured 2-amino 3-hydroxy enamide that lactonizes to furnish the dialkylamino-5H-furan-2-one 195 (Scheme 78). 

Hydroxy-l-oxo-2-phenylpropyl) PhCH(CH20H)C0-[(Aminocarbonyl)amino] HjNCONH-Carbonyldiimino, -NHCONH-(1-Oxopentyl) H3C(CH2)3CO-... 

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