ChemInform Abstract: HETEROADAMANTANES AND THEIR DERIVATIVES. 3. SYNTHESIS OF 5‐(METHOXYCARBONYL)‐6‐HYDROXY‐1,3‐DIAZAADAMANTANE

Кузнецов, А. И.; Boiko, I. P.; Sokolova, T. D.; Basargin, E. B.; Unkovskii, B. V.

doi:10.1002/chin.198540199

Chemischer Informationsdienst

1985

DOI: 10.1002/chin.198540199

|View full text |Cite

ChemInform Abstract: HETEROADAMANTANES AND THEIR DERIVATIVES. 3. SYNTHESIS OF 5‐(METHOXYCARBONYL)‐6‐HYDROXY‐1,3‐DIAZAADAMANTANE

А. И. Кузнецов¹,

I. P. Boiko²,

T. D. Sokolova³

et al.

Abstract: Der 4‐Phenylthio‐3‐oxobuttersäuremethylester (I) reagiert mit Ammoniumacetat, Ammoniumcarbonat und Paraformaldehßtd zu dem Phenylthiodiazaadamantancarbonsäureester (II).

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2008

2012

Publication Types

Select...

Article2

Relationship

Self Cite1

Independent1

Authors

Journals

Cited by 2 publications

(2 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Desulfurization of 1-phenylsulfanyl-3,6-diazahomoadamantane (V) by heating over Raney nickel according to the procedure described in [6,7] gave previously unknown unsubstituted 3,6-diazahomoadamantane (VI) [8] which was isolated as a readily sublimable white crystalline substance with mp 250-251°C.…”

mentioning

confidence: 99%

Synthesis of 3,6-diazahomoadamantane

et al. 2012

Self Cite

View full text Add to dashboard Cite

Condensation of 1-phenylsulfanylpropan-2-one with 1, 3,6,8-tetraazatricyclo[4.4.1.1 3,8 ]dodecane gave 1-phenylsulfanyl-3,6-diazahomoadamantan-9-one which was reduced to 1-phenylsulfanyl-3,6-diazahomoadamantane, and the latter was subjected to desulfurization over Raney nickel to obtain previously unknown 3,6-diazahomoadamantane. Heating of 9-phenyl-3,6-diazahomoadamantan-9-ols with Raney nickel resulted in reduction of the hydroxy group with formation of 9-phenyl-3,6-diazahomoadamantanes.By condensation of methyl ketones with 1,3,6,8-tetraazatricyclo[4.4.1.1 3,8 ]dodecane [1] and subsequent Wolff-Kishner reduction of the resulting 3,6-diazahomoadamantan-9-ones we obtained a number of 3,6-diazahomoadamantane derivatives substituted at the bridgehead position [2][3][4]. In the present communication we report on the synthesis of 3,6-diazahomoadamantane in a similar way. For this purpose, as initial ketone we used 1-phenylsulfanylpropan-2-one (I); its condensation with 1,3,6,8-tetraazatricyclo-[4.4.1.1 3,8 ]dodecane in propan-2-ol afforded more than 60% of 1-phenylsulfanyl-3,6-diazahomoadamantan-9-one (II) (Scheme 1). δ C 65.63 and 59.45 ppm from four bridging methylene carbon atoms.Ketone II was reduced to 1-phenylsulfanyl-3,6-diazahomoadamantane (V) in two ways: (1) through 1-phenylsulfanyl-3,6-diazahomoadamantan-9-one hydrazone (III) according to Wolff-Kishner and (2) by reduction of 1-phenylsulfanyl-3,6-diazahomoadamantan-9-one p-tolylsulfonylhydrazone (IV) with sodium tetrahydridoborate in acetic acid [5] (Scheme 2). Desulfurization of 1-phenylsulfanyl-3,6-diazahomoadamantane (V) by heating over Raney nickel according to the procedure described in [6,7] gave previously unknown unsubstituted 3,6-diazahomoadamantane (VI) [8] which was isolated as a readily sublimable white crystalline substance with mp 250-251°C.In the 1 H NMR spectrum of diazahomoadamantane VI, the NCH 2 CH 2 N ethylene fragment gave rise to

show abstract

mentioning

confidence: 99%

Synthesis of 3,6-diazahomoadamantane

et al. 2012

Self Cite

View full text Add to dashboard Cite

show abstract

“…R 1 , R 2 , R 3 , and X are identified in Table 1. 5-Methyl-7-isopropyl-6-oxo-1,3-diazaadamantane (III) was prepared using the Mannich reaction between ethylisobutylketone and urotropine in acid conditions. 5-Methyl-7-isopropyl-(VI), 5,7-diethyl-(VII), and 5,7-diisopropyl-6-hydroxy-1,3,-diazaadamantanes (VIII) were prepared by reduction of the carbonyl groups of the corresponding 6-oxo-1,3-diazaadamantanes [3] with NaBH 4 . 2-Substituted 1,3-diazaadamantane derivatives (XI -XX) were synthe-sized by condensation of the corresponding 1,5-dialkyl-3,7diazabicyclo[3.3.1]nonanes with various aldehydes.…”

mentioning

confidence: 99%

Synthesis and reactions of polyhedral compounds. 29. Synthesis and antibacterial activity of 1,3-diazaadamantane derivatives

et al. 2008

View full text Add to dashboard Cite

The antibacterial activity of 1,3-diazaadamantane derivatives was studied; a degree of relationship between chemical structure and the antibacterial activity of the compounds synthesized was identified. The results obtained here showed that some of the study compounds were active against Gram-positive and Gram-negative microorganisms. 180091-150X/08/4201-0018 XVIII 4.65 s (1H, NCHN), 3.48 d (1H, J 5.4, OCH), 3.30 dd (1H, J 1 12.8, J 2 2.6, CH 2 N), 3.03 dd (1H, J 1 13.1, J 2 2.1, CH 2 N), 2.98 dd (1H, J 1 13.1, J 2 2.6, CH 2 N), 2.87 dd (1H, J 1 13.0, J 2 2.0, CH 2 N), 2.77 dd (1H, J 1 13.2, J 2 3.0, CH 2 N), 2.71 dd (1H, J 1 12.8, J 2 1.3, CH 2 N), 2.53 -2.45 m (2H, CH 2 N). 7.01 d (1H, J 1.0, 2'-H), 6.99 d (1H, J 1.0, 6¢-H), 6.70 d (1H, J 7.9, 5¢-H), 5.92 s (2H, OCH 2 O), 4.24 d (1H, J 5.4, OH), 1.31 dq (1H, J 1 13.8, J 2 7.5, CH 2 ), 1.00 -1.21 m (2H, CH 2 ), 0.73 m (1H, CH 2 ), 0.83 t (3H, J 7.5, CH 3 ), 0.65 t (3H, J 7.2, CH 3 ). XIX 4.74 s (1H, NCHN), 3.48 dt (1H, J 1 5.4, J 2 1.4, OCH), 3.23 dd (1H, J 1 12.8, J 2 2.9, CH 2 N), 2.99 dd (1H, J 1 13.0, J 2 2.4, CH 2 N), 2.93 dd (1H, J 1 13.0, J 2 2.4, CH 2 N), 2.90 dd (1H, J 1 13.0, J 2 2.9, CH 2 N), 2.84 dd (1H, J 1 13.0, J 2 3.1, CH 2 N), 2.68 dt (1H, J 1 12.9, J 2 1.6, CH 2 N), 2.61 dt (1H, J 1 13.1, J 2 1.6, CH 2 N), 2.54 dd (1H, J 1 13.2, J 2 3.2, CH 2 N). 7.36 d (1H, J 1.7, 5¢-H), 6.32 dd (1H, J 1 3.2, J 2 1.7, 4¢-H), 6.21 d (1H, J 3.2, 3¢-H), 4.33 d (1H, J 5.4, OH), 1.30 dq (1H, J 1 13.8, J 2 7.6, CH 2 ), 1.18 dq (1H, J 1 13.8, J 2 7.3, CH 2 ), 1.04 dq (1H, J 1 13.8, J 2 7.3, CH 2 ), 0.83 dq (1H, J 1 13.8, J 2 7.6, CH 2 ), 0.82 t (3H, J 7.6, CH 3 ), 0.68 t (3H, J 7.3, CH 3 ). XX 5.03 s (1H, NCHN), 3.54 d (1H, J 5.4, OCH), 3.34 dd (1H, J 1 12.8, J 2 3.1, CH 2 N), 3.15 dd (1H, J 1 13.0, J 2 2.3, CH 2 N), 3.02 dd (1H, J 1 13.0, J 2 3.1, CH 2 N), 2.98 dd (1H, J 1 13.1, J 2 2.2, CH 2 N), 2.90 -2.81 m (2H, CH 2 N), 2.69 dt (1H, J 1 12.8, J 2 1.4, CH 2 N), 2.58 dd (1H, J1 13.0, J 2 3.1, CH 2 N). 10.27 br s (1H, NH), 7.88 d (1H, J 8.1, 7¢-H), 7.12 d (1H, J 7.9, 4¢-H), 6.85 ddd (1H, J 1 7.8, J 2 7.1, J 3 1.3, 6¢-H), 6.75 ddd (1H, J 1 8.1, J 2 7.1, J 3 1.3, 5¢-H), 4.12 d (1H, J 5.4, OH), 2.46 s (3H, 2¢-CH 3 ), 1.31 dq (1H, J 1 13.9, J 2 7.5, CH 2 ), 1.23 -1.03 m (2H, CH 2 ), 0.68 m (1H, CH 2 ), 0.85 t (3H, J 7.5, CH 3 ), 0.65 t (3H, J 7.5, CH 3 ).* Prime marks identify protons of aromatic groups at position 2 of the 1,3-diazaadamantane nucleus.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

ChemInform Abstract: HETEROADAMANTANES AND THEIR DERIVATIVES. 3. SYNTHESIS OF 5‐(METHOXYCARBONYL)‐6‐HYDROXY‐1,3‐DIAZAADAMANTANE

Abstract: Der 4‐Phenylthio‐3‐oxobuttersäuremethylester (I) reagiert mit Ammoniumacetat, Ammoniumcarbonat und Paraformaldehßtd zu dem Phenylthiodiazaadamantancarbonsäureester (II).

Cited by 2 publications

References 0 publications

Synthesis of 3,6-diazahomoadamantane

Synthesis of 3,6-diazahomoadamantane

Synthesis and reactions of polyhedral compounds. 29. Synthesis and antibacterial activity of 1,3-diazaadamantane derivatives

Contact Info

Product

Resources

About