Studies on heterocyclic analogues of azulene. Part 2. Cycloaddition reactions of aza-analogues of azulene with dimethyl acetylenedicarboxylate: intermediacy of a 1,8-dipolar species

1978 ◽  
pp. 429 ◽  
Author(s):  
Noritaka Abe ◽  
Yasuko Tanaka ◽  
Tarozaemon Nishiwaki
Keyword(s):  
Cycloaddition Reactions ◽  
Dimethyl Acetylenedicarboxylate

Cycloaddition reactions. Addition of dimethyl acetylenedicarboxylate to 1-dimethylaminoindene

1970 ◽  
Vol 48 (11) ◽  
pp. 1633-1638 ◽  
Author(s):  
Terrence W. Doyle
Keyword(s):  
Ring Opening ◽  
Cycloaddition Reactions ◽  
Dimethyl Acetylenedicarboxylate ◽  
Reaction Conditions

The cycloaddition of 1-dimethylaminoindene (2) to dimethyl acetylenedicarboxylate to form a fused cyclobutene system 3 is discussed. Compound 3 underwent two modes of ring opening to yield either the indene–maleate system 4 or the benzocycloheptatriene system 5 depending on reaction conditions. The synthesis of a number of multifunctional benzotropones from 5 is discussed.

scholarly journals Huisgen [3 + 2] Dipolar Cycloadditions of Phthalazinium Ylides to Activated Symmetric and Non-Symmetric Alkynes

Molecules ◽  
2020 ◽  
Vol 25 (19) ◽  
pp. 4416
Author(s):  
Vasilichia Antoci ◽  
Costel Moldoveanu ◽  
Ramona Danac ◽  
Violeta Mangalagiu ◽  
Gheorghita Zbancioc
Keyword(s):  
Reaction Time ◽  
Comparative Study ◽  
Cycloaddition Reaction ◽  
Environmentally Friendly ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Dimethyl Acetylenedicarboxylate ◽  
Thermal Heating ◽  
Dipolar Cycloadditions ◽  
Methyl Propiolate

We present herein a straightforward and efficient pathway for the synthesis of pyrrolophthalazine cycloadducts via Huisgen [3 + 2] dipolar cycloaddition reactions of phthalazinium ylides to methyl propiolate or dimethyl acetylenedicarboxylate (DMAD). A thoroughly comparative study concerning the efficiency of synthesis, conventional thermal heating (TH) versus microwave (MW) and ultrasound (US) irradiation, has been performed. The cycloaddition reactions of phthalazinium ylides to methyl propiolate occur regiospecific, with a single regioisomer being obtained. Under conventional TH, the cycloaddition reaction of phthalazinium ylides with DMAD occurs to a mixture of inseparable partial and fully aromatized pyrrolophthalazine cycloadducts, while MW or US irradiation are leading only to fully aromatized compounds, with the reactions becoming selective. A feasible mechanism for formation of fully aromatized compounds is presented. Besides selectivity, it has to be noticed that the reaction setup under MW or US irradiation offer a number of other certain advantages: higher yields, decreasing of the amount of used solvent comparative with TH, decreasing of the reaction time from hours to minutes and decreasing of the consumed energy; consequently, these reactions could be considered environmentally friendly.

Cycloaddition Reactions of [1,2]Dithiolo[1,2]dithiole Derivatives with Dimethyl Acetylenedicarboxylate: Formation of New Bi-, Tri- and Tetracyclic Thiopyran Derivatives

Synthesis ◽  
1994 ◽  
Vol 1994 (10) ◽  
pp. 1067-1071 ◽  
Author(s):  
E. Fanghänel ◽  
T. Palmer ◽  
J. Kersten ◽  
R. Ludwigs ◽  
K. Peters ◽  
...  
Keyword(s):  
Cycloaddition Reactions ◽  
Dimethyl Acetylenedicarboxylate

Cycloaddition Reactions of 3-Dimethylamino-1-methyl-1,2,4-triazinium-5-olates With Dimethyl Acetylenedicarboxylate

1995 ◽  
Vol 48 (6) ◽  
pp. 1175 ◽  
Author(s):  
RP Musgrave ◽  
NW Jacobsen ◽  
G Bourne ◽  
CHL Kennard ◽  
G Smith ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Single Crystal ◽  
Cycloaddition Reactions ◽  
Dimethyl Acetylenedicarboxylate ◽  
X Ray ◽  
Structure Determinations ◽  
Mechanism Of The Reaction

The cycloaddition reactions of some 3-dimethylamino-1-methyl-1,2,4-triazinium-5-olates (1) with dimethyl acetylenedicarboxylate ( dmad ) were studied. The products in all cases were found tobe dimethyl 4-dimethylamino-1-methyl-6-oxo-1,3a,6,6a-tetrahydropyrrolo[3,4-c]pyrazole-3,3a-dicarboxylate derivatives (2). The structure determinations were carried out by 1H and 13C n.m.r. and mass spectrometry, and for one derivative by single-crystal X-ray diffractometry. The mechanism of the reaction is also discussed.

The Cycloaddition Reactions of Some 7-Alkylidenecycloocta-1,3,5-trienes

1990 ◽  
Vol 43 (3) ◽  
pp. 463 ◽  
Author(s):  
PH Ferber ◽  
GE Gream ◽  
PK Kirkbride ◽  
ERT Tiekink
Keyword(s):  
Maleic Anhydride ◽  
Cycloaddition Reactions ◽  
Dimethyl Acetylenedicarboxylate ◽  
Chlorosulfonyl Isocyanate ◽  
Diethyl Azodicarboxylate

A number of 7-alkylidenecycloocta-1,3,5-trienes, all unstable, yield novel π8+π2 cycloadducts with a range of π2-addends. The reactions of 7-methylenecycloocta-1,3,5-triene with ethene-tetracarbonitrile, 4- phenyl-1,2,4-triazoline-3,5-dione, diethyl azodicarboxylate and chlorosulfonyl isocyanate are described. The tetraene did not react with maleic anhydride or dimethyl acetylenedicarboxylate. As well, the reactions of 1,3,5-trimethyl-7-methylenecycloocta-1,3,5-triene, 2,9a- dihydro-1H-cyclopentacyclooctene and 1,2,3,10a- tetrahydrobenzocyclooctene with ethenetetracarbonitrile and of 7- isopropylidenecycloocta-1,3,5-triene with 4-phenyl-1,2,4-triazoline- 3,5-dione are discussed. The intermediacy of homotropylium zwitterions in the reactions is postulated.

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