• Bulletin of the Korean Chemical Society
• /
• 제31권3호
• /
• pp.694-696
• /
• 2010

• 약학회지
• /
• 제44권4호
• /
• pp.325-333
• /
• 2000

The 1,3-dipolar cycloaddition reaction of the quinoxaline 4-oxides 2 with 2-chloroacrylonitrile gave the 2,3-dihydro-1H-1,2-diazepino[3,4-b]quinoxalines 3, which were converted into the 2,3,4,6-tetrahydro-1H-1,2-diazepino[3,4-b]quinoxalines 5-7. The reaction of compounds 3 with selenium dioxide in acetic acid/water resulted in ring transformation to give the 1,4-dihydro-4-oxopyridazino[3,4-b]quinoxalines 8.

• 대한화학회지
• /
• 제30권2호
• /
• pp.243-247
• /
• 1986

호모프탈산 무수물(1또는 2)과 디에틸 아조디카르복시산 및 에틸 아릴메티리덴카르밤산과의 고리화첨가반응을 검토하였다. 전자의 반응에서는 2,3--디에톡시카르보닐-2,3-디히드로-1-히드록시프탈라진들(3 및 4)이 생성되었으며, 후자의 반응에서는 3-아릴-4카르복시-2-에톡시카르보닐-3,4-디히드로-1(2H)-이소퀴놀린온들(5~10)이 생성되었다.

• Bulletin of the Korean Chemical Society
• /
• 제17권10호
• /
• pp.909-918
• /
• 1996

Syntheses of carbapenam skeletons were achieved from 1,3-propanediol through 1,3-dipolar cycloaddition. 3-(Tetrahydropyran-2-yloxy)-(10) and 3-(t-butyldimethylsilyloxy) propanal (13) were obtained from 1,3-propanediol. 3-Hydroxypropanals (10, 13, 14) were reacted with N-hydroxyglycine esters to give C-(2-hydroxyethyl)-N-alkoxycarbonylmethylnitrones (15a-15d). 1,3-Dipolar cycloaddition of the nitrones with methyl acrylate or ethyl crotonate gave 3-(2-hydroxyethyl)isoxazolidines (16a-16b, 17a-17b, 18, 19a-19b). 3-(2-Hydroxyethyl)isoxazolidines (17a, 17c, 19a, 19b) were converted to 3-(2-iodoethyl)isoxazolidines (21a-21d) or 3-phenylthiocarbonylmethylisoxazolidines (25a-25d) which were cyclized to give 2-oxa-1-azabicyclo[3.3.0]octanedicarboxylates (22a-22d, 26a-26d). 2-Oxa-1-azabicyclo[3.3.0]octane-4,8-dicarboxylates (22c-22d, 26c-26d) were transformed to 6-(l-hydroxyethyl)carbapenam-3-carboxylates (30a-30b, 31a-31b).

• Bulletin of the Korean Chemical Society
• /
• 제17권11호
• /
• pp.985-987
• /
• 1996

• Bulletin of the Korean Chemical Society
• /
• 제19권10호
• /
• pp.1080-1083
• /
• 1998

An efficient method for construction of 2-arylfiirans has been developed by ceric(IV) ammonium nitratemediated oxidative cycloaddition of cyclic and acyclic 1,3-dicarbonyl compounds to several alkynes. Reactions of 1,3-cyclohexanedione, 1,3-cyclopentanedione, and 2,4-pentanedione with several alkynes furnish 2-arylfurans in 26-75% yields. Extension of this technology to more complex 4-hydroxy-2-quinolone and 3-hydroxy-lH-phenalen-l-one with phenylacetylene also affords furoquinolinone and ftirophenalenone derivative in moderate yields. Reaction of 4-hydroxycoumarins with phenylacetylene give linear and angular furocoumarin derivatives as a mixture of regioisomer in good yields. The mechanistic pathway for the formation of 2-arylfurans has been also described.

• Bulletin of the Korean Chemical Society
• /
• 제29권8호
• /
• pp.1561-1564
• /
• 2008

Although the use of Cu(II) salts as catalysts without reductants is limited in the cycloaddition of acetylenes with azides, the catalytic system employing average 10 nm CuO(II) nanoparticles in the absence of reductants shows good catalytic activity to form 1,4-disubstituted 1,2,3-triazoles even in wet THF as well as water. It is also noticeable that CuO(II) nanoparticle catalysts can be recycled with consistent activity. A range of alkynes and azides were subject to the optimized CuO(II) nanoparticle-catalyzed cycloaddition reaction conditions to afford the desired products in good yields.

• 대한화학회지
• /
• 제21권3호
• /
• pp.155-160
• /
• 1977

경쟁 1,2-와 1,4-고리화첨가반응에 대한 frontier 분자궤도와 전전자에너지의 상관도를 작도하고 이 상관도에 의해서 반응기구를 설명할 수 있었다. 고찰해서 유도된 중요 결론은 다음과 같다. 1) HO와 LU사이에 교차가 일어나지 않았다. 그러므로 반응은 열반응이다. 2) diradical을 경유하는 이단계기구가 일단계기구 보다 에너지장벽으로 미루어 보아 유리하다. 3) [2+2]와 [2+4] 고리화첨가물의 생성물분포를 예측할 수 있다.

• Archives of Pharmacal Research
• /
• 제15권4호
• /
• pp.292-297
• /
• 1992

Coupling of naphthacylpyridinium bromide 2 [1-(2-naphthyl) ethanone-2-pyridinium bromide] with N-nitrosoacetarylamides afforded C-(2-naphthoyl)-N-arylmethanohydrazonoylpyridinium bromides 3A-C. Treatment of 3A-C with base afforded the corresponding tetrazines 6A-C. Cycloaddition of nitrilimines 5A-C to N-arylmaleimides, acrylonitrile, ethyl acrylate, acrylamide, fumaronitrile, $\alpha$-cyanocinnamonitriles, ethyl $\alpha$-cyano-p-nitrocinnamates and $\alpha$-cyano-p-nitrocinnamamide afforded the corresponding cycloadducts 7-14, respectively. The cycloadducts 11-14 undergo a facile thermal elimination of hydrogen cyanide to give the corresponding pyrazoles 18-21 respectively.

• 한국군사과학기술학회지
• /
• 제18권6호
• /
• pp.736-742
• /
• 2015

The effect of pressure on 1,3-dipolar cycloaddtion has been studied by means of FT-IR and NMR spectroscopy. Pressure accelerates 1,3-dipolar cycloaddition without solvent or catalyst. This simple and inexpensive method eliminates the need for work-up or purification. The method is expected to be applied to the synthesis of binders for solid rocket propellants.