2- Amino-3-aminocarbonyl

Gegenuber Zink/Saure bzw. Zinn(II)-chlorid/Saure sind Furazane stabil sie lassen sich daher aus den zugrundeliegenden Furoxanen herstellen (s. S. 666). 4-Amino-3-aminocarbonyl-furazane werden dagegen mit Zinkstaub in Ameisensaure zu 4-Amino-5-aminocarbonyl-imidazolen umgeselzt311 ... 

The insertion of a methyl or a benzyl group into the 3 position of 4-amino-5-aminocarbonyl-1,2,3-triazole affects the spectrum very little, and a phenyl group is even slightly hypsochromic (see 4-amino-5-aminocarbonyl-3-m-tolyl-... 

As an alternative to the use of sodium, hydrogenation in ethanolic ammonia over palladium is effective. Thus 4-amino-5-aminocarbonyl-3-benzyl-l-methyl-l,2,3-triazolium toluene-p-sulfonate gave 4-amino-l-methyltriazole-5-carboxamide (75°C, 4 atm, 3 hr, 82%) [68JCS(C)344 72JCS(P1)461]. 4-Amino-3-benzyltriazole-5-fV-butylcarboxamidine was similarly debenzylated (70 C, 3 hr, 85%) [74JCS(P1)2030]. 

Amino-5-cyan-1679, 4-Amino-5-aminocarbonyl-1263,2214,2526 und 4-Amino-5-(amino-hydr-oximino-methyl)-lH-pyrazole2214 cyclisieren mit C-l-Bausteinen zu 1 H-pyrazol-Derivate reagieren zu 2H-[Pg.686]

Wird die Cyclokondensation mit Benzoesaure in Polyphosphorsaure durchgefiihrt, entsteht z.B. aus 4-Amino-5-aminocarbonyl-l,3-dimethyl-lH-pyrazol l,3-Dimethyl-7-hydroxy-5-phe-nyl-lH-(j)yrazolo[4,3-d]pyrimidin ) (Schmp. 273-274°) (weitere Beispiele vgl. Lit.2000). 

Amino-4-aminocarbonyl-2-mcrcapto- 20 4-Amino-5-aminocarbonyl-2-morpholino-... 

On the other hand, unsaturated /J-aminoamides have been obtained by Ni(II)-promoted stoichiometric oxidative amino-aminocarbonylation of substituted allenes [60] (Eq. 19). 

The catalytic oxidative carbonylation of allene with PdCb and CuCh in MeOH affords methyl a-methoxymethacrylate (559)[499]. The intramolecular oxidative aminocarbonylation of the 6-aminoallene 560 affords the unsaturated J-amino ester 561. The reaction has been applied to the enantioselective synthesis of pumiliotoxin (562)[500]. A similar intramolecular oxycarbonyla-tion of 6-hydroxyallenes affords 2-(2-tetrahydrofuranyl)acrylates[501]. 

The main reaction of this type has been the reductive cyclization of nitropyridine derivatives carrying an o-amino ester or o-aminocarbonyl substituent. These cyclize in situ via the o-diamino derivative to give pyridopyrazines of known constitution, either for establishment of structure of products obtained in the ambiguous Isay synthesis (see Section 2.15.15.6.1), or in the synthesis of aza analogues of biologically active molecules. 

Cyclization of l-(A -substituted aminocarbonyl)-3-[(tert-butoxycarbonyl) amino]- and -3- [Ai -(tert-butoxycarbonyl)tryptophyl]amino -2-(ethoxycar-bonylmethyl)piperidines (e.g. 188) on the action of NaH gave 2-substituted 5-(substituted amino)perhydropyrido[l,2-c]pyrimidine-l,3-diones (e.g. 159 and 189) (97JMC3402, 97MIP16, 98MI63, 0UMC2219). Cyclization could be also carried out in the presence of DBU (01JMC2219). 

Chemical Name 2,2 -[ ([4-[(Aminocarbonyl)amino] phenyl] arsinidene] bis(thio)] bis (acetic acid]... 

Selektive Reduktionen der Carboxy-Gruppe hangen von der Struktur der Aminocarbonyl-Gruppe ab und sind nur selten moglich3. In der Regel werden also Amino-alkohole erhalten4 z.B. ... 

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 ... 

Athoxycarbonyl- 600 2-(Athoxymethylen-amino)- 351 2-Alkylthio-4,5-dihydro- 347 2-Amino- 351 2-Aminocarbonyl- 600 2-Benzylaminocarbonyl- 600 2-Carboxy- 600... 

Aryl-4,5-dihydro- 262 1-Alkyl-4,5-dihydro- 262 5-Amino-4-aminocarbonyl-2,3-dihydro- 597... 

CN [25-[2a,3a(Z)]]-[[[2-[[2-[[(aminocarbonyl)oxy]methyl]-4-oxo-l-sulfo-3-azetidinyl]amino]-l-(2-amino-4-thiazolyl)-2-oxoethylidene]amino]oxy]acetic acid... 

CN [6R-[6a,7P(R )]]-4-(aminocarbonyl)-l-[[2-carboxy-8-oxo-7-[(phenylsulfoacetyl)amino]-5-thia-l-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]pyridinium hydroxide inner salt... 

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... 

CiiHijNO, 3SS4J-4J-7) see Carboquone 2-(2-aminocarbonyloxy-l-methoxyethyl)-S-methyl-hydroquinone dimethyl ether (CjjHiijNOj 38843-63-9) see Carboquone [6U-[6a,7a,7(iJ )])-3-[[(aminocarbonyl)oxyJmethyl]-7-[[5-carboxy-S-[[(4-methylphenyl)sulfonyl]amino]-l-oxo-pentyl]amino]-7-methoxy-8-oxo-5-thia-l-azabicy-clo[4.2.01oct-2-ene-2-carboxylic acid compd. with A-cyclohexylcyclohexanamine (1 1)... 

C33H51N5O11S2 83292-23-.3) see Cefoxitin [6/(-[6a,7a,7(/ )]]-3-[[(aminocarbonyl)oxy]methyll-7-[[6-(diphenylmethoxy)-l,6-dioxo -S-[[(2,2,2-trichloroethoxy)-carbonyl]aminolhexyl]amino]-7-methoxy-8-oxo-S-thia-l-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylme-thyl ester... 

Earlier, urea was reacted with EMME in the presence of sodium ethylate in ethanol at ambient temperature for 7 days to give (aminocarbonyl-amino)methylenemalonate (216) in 22% yield (52JA4267). (Aminocar-bonylamino)methylenemalonate (216) was not obtained when urea and EMME were heated at 140°C (07MI1). 

Aminocarbonyl)amino)sulfonyl) benzoate, see Sulfometuron-methvl... 

Soil. In unsterilized soils, 58% of C-labeled sulfometuron-methyl degraded after 24 wk. Metabolites identified were 2,3-dihydro-3-oxobenzisosulfonazole (saccharin), methyl-2-(amino-sulfonyl) benzoate, 2-aminosulfonyl benzoic acid, 2-(((aminocarbonyl)amino)sulfonyl) benzoate, and [ C]carbon dioxide. The rate of degradation in aerobic soils was primarily dependent upon pH and soil type (Anderson and Dulka, 1985). The reported half-life in soil was approximately 4 wk (Hartley and Kidd, 1987). 

T. Komano worked with him. The work accomplished at that time included the following N-debenzyloxycarbonylation of 1,3,4,6-tetra-0-acetyl-2-(benzyloxycarbonyl)amino-2-deoxy-D-hexopyranoses in the conversion of a,/3-acetoxy to glycosyl bromide (1961) oxidative cleavages of 1,2-diamino sugars and their significance in the mechanism of the aminocarbonyl reactions (1962) and synthesis of 2-amino-2-deoxy-/3-o-glucosides via 3,4,6-tri-D-acetyl-2-benzylsulfonamido-2-deoxy-a-D-glu-copyranosyl bromide (1962). 

Other interesting examples of these amino-exchange reactions are the conversion of 3-aminocarbonyl-4-R-l-(2,4-dinitrophenyl)pyridinium salt (2) into 3-aminocarbonyl-4-R-l-cbutylpyridinium salt by Cbutylamine (82RTC342) and the preparation of l-(pentadeuteriophenyl)-3-amino-carbonyl-4-deuteriopyridinium salt from 3-aminocarbonyl-l-(2,4-dinitro-phenyl)-4-deuteriopyridinium salt (2, R = D) with pentadeuterioaniline (84T433) (Scheme IIL2). 

The thermally induced Cornforth rearrangement can be rationalized by postulating the dicarbonylnitrile ylid 103 as intermediate. It is especially the natures of the substituents R and R" that determine the direction of the rearrangement. For example, heating of 5-alkoxy-4-(aminocarbonyl)oxazole (102, R = OAlkyl, R" = NR2) readily gives in a good yield rearrangement into the isomeric 5-(substituted amino)-4-(alkoxycarbonyl) oxazole (104, R = OAlkyl, R" = NR2) (Scheme IV.40). 

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-... 

Imipenem undergoes enzymatic inactivation in the kidneys. In order to avoid this problem, it is used in a 1 1 ratio in combination with cilastatin—the sodium salt of [/ -[/ ,5 -(Z)]]-7-[(2-amino-2-carboxyethyl)thio]-2-[[(2,2-dimethylcyclopropyl)aminocarbonyl-2-heptenoic acid... 

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