Synthesis of benzannelated cycl(3.2.2)azine: Benzo(g)cycl(3.2.2)azine.

Tominaga, Yoshinori; Gotou, H.; Oniyama, Yukio; Nishimura, Yuko; Matsuda, Yoshiro

doi:10.1248/cpb.33.3038

Cited by 15 publications

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“…Tominaga showed that indolizines 47a , b having annelated benzene ring across the bond C7–C8 underwent [8+2] cycloaddition forming benzo[g]cycl[3.2.2]azines [ 29 , 67 ], Scheme 22 .…”

Section: Cycloaddition To Benzoindolizines: Synthesis Of Benzo Dermentioning

confidence: 99%

Indolizines and Their Hetero/Benzo Derivatives in Reactions of [8+2] Cycloaddition

Бабаев

Шадрин

2021

Molecules

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Peculiarities of [8+2] cycloaddition of acetylenes to indolizines are reviewed. Especially mentioned are indolizines with leaving groups at positions 3 and 5. Cycloaddition to aza- and benzo derivatives are reviewed, as well as 1,10-cyclizations and processes leading to cyclazines where indolizines are intermediates. Mechanistic features (adducts and cycloadducts) and theoretical aspects (one- or two-steps mechanism) are reviewed.

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“…Tominaga showed that indolizines 47a , b having annelated benzene ring across the bond C7–C8 underwent [8+2] cycloaddition forming benzo[g]cycl[3.2.2]azines [ 29 , 67 ], Scheme 22 .…”

Section: Cycloaddition To Benzoindolizines: Synthesis Of Benzo Dermentioning

confidence: 99%

Indolizines and Their Hetero/Benzo Derivatives in Reactions of [8+2] Cycloaddition

Бабаев

Шадрин

2021

Molecules

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“…During successive treatment with carbon disulfide and dimethyl sulfate, the ylide (XL), which is a'nucleophile, gives the salt (LI) [128,129], and this reacts with the C-nucleophilic nitromethane. The further elimination of the ready leaving groups and decarboxylation lead to compound (LII): [131,132].…”

Section: XLVIImentioning

confidence: 99%

Pyrrolo[2,1-a]isoquinolines (review)

Михайловский¹,

Shklyaev²

1997

Chem Heterocycl Compd

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“…I n wiierigern Methanol kann es leicht alkyliert werden, wobei im Falle der Methylierung das Keten-S,S-acetal gebildet wird, das mit Aminen die Keten-S,N-bzw. -N,N-acetale entstehen liil3t [116,117]. …”

Section: A-nitro-curbanionenunclassified

Umsetzungen von α‐Heterocarbanionen mit schwefelhaltigen Heterokumulenen

Augustin

Dölling

1990

Zeitschrift fuer Chemie

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Martin-Lutlier-UniversitatHallc-Wittenberg, Sektion Chemie, 0-4010 Halle (Saale) Sulnlluttry Cyclic or noncyclic a-heteroearbanions, deriued f r o m CH-ucidic compounds with different buses through deprotution, reuct with rnuny electrophiles. a-Oxu-, a-thiu-, a-uzau?Ld a-phosphucurbunions ujjord with sulphur-containing iheterocumulenes (ctrrbondisulphide, isothiocyonntes) to intermediutes, yielding with electrophiles dif'jereibt ketene-S, S-und -S, N-ucetules or heterocyclic compounds ujter cycl isution. 131 132 130 131 133 135 136 137 138 PhNCS 140 139 a-Methylen-phosphane 130 bzw. -phosphanoxide 136 lassen sich leicht mit Basen zu a-Phospha-carbanionen deprotonieren, rnit CS, dithiorarboxylieren und zu den Dithiocarbonsaureestern 132 und 139, aber auch Keten-S,S-acetalen 158 bzw. -S,N-acetalen 130 umsetzen [119-1%]. l l i t h i o c~l r 6 o~y l i e r~n~ van Stanna-AnionenDas Triphenyl-zinn-lithium 141 reagiert in T H F mit CS, iiber 142 zu Triphenyl-zinn-dithiocarbonsaureester 143 [128, 1291. 401.

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Synthesis of benzannelated cycl(3.2.2)azine: Benzo(g)cycl(3.2.2)azine.

Cited by 15 publications

References 0 publications

Indolizines and Their Hetero/Benzo Derivatives in Reactions of [8+2] Cycloaddition

Indolizines and Their Hetero/Benzo Derivatives in Reactions of [8+2] Cycloaddition

Pyrrolo[2,1-a]isoquinolines (review)

Umsetzungen von α‐Heterocarbanionen mit schwefelhaltigen Heterokumulenen

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