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the insertion of a cannula or tube into a hollow body organ (同)canulation, cannulization, cannulisation, canulization, canulisation, intubation

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/12/06 17:22:55」(JST)

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Annulation (derived from annular, occasionally annelation) in organic chemistry is a chemical reaction in which a new ring is constructed on another molecule (often another ring).^[1]

Examples are the Robinson annulation, Danheiser annulation and certain cycloadditions. Annular molecules are constructed from side-on condensed cyclic segments, for example helicenes and acenes. In transannulation a bicyclic molecule is created by intramolecular carbon-carbon bond formation in a large monocyclic ring. An example is the samarium(II) iodide induced ketone - alkene cyclization of 5-methylenecyclooctanone which proceeds through a ketyl intermediate:^[2]

Benzannulation

The term benzannulated compounds refers to derivatives of cyclic compounds (usually aromatic) which are fused to a benzene ring. Examples are listed in the table below:

Benzannulated derivative	Source of cyclic compound
Benzopyrene	Pyrene
Quinoline	Pyridine
Isoquinoline	Pyridine
Chromene	Pyran
Isochromene	Pyran
Indole	Pyrrole
Isoindole	Pyrrole
Benzofuran	Furan
Isobenzofuran	Furan
Benzimidazole	Imidazole

Transannular interaction

A transannular interaction in chemistry is any chemical interaction (favorable or nonfavorable) between different non-bonding molecular groups in a large ring or macrocycle.^[3] See for an example the molecule atrane.

References

^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "annulation". IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "annelation".
^ Construction of Bicyclic Ring Systems via a Transannular SmI2-Mediated Ketone-Olefin Cyclization StrategyGary A. Molander, Barbara Czakó, and Michael Rheam J. Org. Chem.; 2007; 72(5) pp 1755 - 1764; (Article) doi:10.1021/jo062292d
^ Experimental evidence in support of transannular interactions in diketones Kata Mlinaric-Majerski, Marijana Vinkovic, Danko Škare, Alan P. Marchand Arkivoc DS-339E 2002 Online Article

English Journal

Synthesis of tetrasubstituted benzenes via rhodium(i)-catalysed ring-opening benzannulation of cyclobutenols with alkynes.

Matsuda T, Miura N.SourceDepartment of Applied Chemistry, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan. mtd@rs.tus.ac.jp.
Organic & biomolecular chemistry.Org Biomol Chem.2013 Jun 4;11(21):3424-7. doi: 10.1039/c3ob40436f. Epub 2013 Mar 28.
A formal [4 + 2] annulation occurs between 1,3-disubstituted cyclobutenols and internal alkynes in the presence of rhodium(i) catalysts to afford 1,2,3,5-tetrasubstituted benzenes. These benzannulation products are generated through dehydration of the initially formed cyclohexadienols.
PMID 23535983

Diversity-oriented synthesis of pyrazolo[4,3-b]indoles by gold-catalysed three-component annulation: application to the development of a new class of CK2 inhibitors.

Hou Z, Oishi S, Suzuki Y, Kure T, Nakanishi I, Hirasawa A, Tsujimoto G, Ohno H, Fujii N.SourceGraduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan. hohno@pharm.kyoto-u.ac.jp nfujii@pharm.kyoto-u.ac.jp.
Organic & biomolecular chemistry.Org Biomol Chem.2013 May 28;11(20):3288-96. doi: 10.1039/c3ob40223a.
Pyrazolo[4,3-b]indole derivatives have been designed as novel CK2 inhibitor compounds based on the binding mode analysis of a previously reported phenylpyrazole-type CK2 inhibitor. A series of pyrazolo[4,3-b]indoles and related dihydropyrazolo[4,3-b]indoles were efficiently prepared from simple star
PMID 23535832

General and Efficient Synthesis of Indoles through Triazene-Directed C-H Annulation.

Wang C, Sun H, Fang Y, Huang Y.SourceKey Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University, Shenzhen Graduate School, Shenzhen (China) http://scbb.szpku.edu.cn/huang.
Angewandte Chemie (International ed. in English).Angew Chem Int Ed Engl.2013 May 27;52(22):5795-8. doi: 10.1002/anie.201301742. Epub 2013 Apr 19.
Unprotected indoles are prepared with the title method, which has a wide scope for alkynes. Excellent regioselectivity was accomplished for aryl-alkyl and alkyl-alkyl disubstituted acetylenes. This reaction features an unusual 1,2 rhodium migration and ring-contraction-triggered NN bond cleavage.
PMID 23606211

Japanese Journal

PALLADIUM-CATALYZED [3+2] ANNULATION OF meso-BROMOPORPHYRINS WITH SILYLACETYLENES AND DESILYLATION OF 8[a]-SILYL-7,8-DEHYDROPURPURIN (Dedicated to Professor Isao Kuwajima on the occasion of his 77th birthday)

Fukui Norihito,Arai Seiji,Shinokubo Hiroshi [他]
Heterocycles : an international journal for reviews and communications in heterocyclic chemistry 90(1), 252-260, 2015-01-01
NAID 40020330181

Alkynoxy Directed C–H Functionalizations: Palladium(0) Catalyzed Annulations of Alkynyl Aryl Ethers with Alkynes

Minami Yasunori,Shiraishi Yuki,Kodama Tatsuro,Kanda Mayuko,Yamada Kotomi,Anami Tomohiro,Hiyama Tamejiro
Bulletin of the Chemical Society of Japan advpub(0), 2015
… Palladium(0)-catalyzed insertion/annulation sequence between aryl silylethynyl ethers and internal alkynes was found to proceed through activation of ortho-C–H bonds assisted by alkynoxy groups and gave stereoselectively (Z)-2-silylmethylenechromenes. … When unsymmetric alkynes are employed, a regioselective annulation takes place, especially those containing aryl and/or bulky substituents. …
NAID 130005088944

Cyanoazulene-based Multistage Redox Systems Prepared from Vinylcyclopropanecarbonitrile and Cyclopentenone via Divinylcyclopropane-rearrangement Approach

Tanino Keiji,Yamada Takumasa,Yoshimura Fumihiko,Suzuki Takanori
Chemistry Letters 43(5), 607-609, 2014
… A series of 4-cyanoazulene derivatives 1–5 were synthesized from 4-cyanohexahydroazulen-1-one, which was efficiently obtained by the annulation of the seven-membered ring on the cyclopentenone skeleton via the divinylcyclopropane rearrangement. …
NAID 130004868100