The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Catalytic asymmetric dipolar cycloadditions of indolyl delocalized metal-allyl species for the enantioselective synthesis of cyclopenta [b]indoles and pyrrolo[1,2-a]indoles》. Authors are Tian, Fei; Yang, Wu-Lin; Ni, Tao; Zhang, Jian; Deng, Wei-Ping.The article about the compound:5-Methoxy-1H-indole-2-carbaldehydecas:21778-81-4,SMILESS:O=CC(N1)=CC2=C1C=CC(OC)=C2).SDS of cas: 21778-81-4. Through the article, more information about this compound (cas:21778-81-4) is conveyed.
Herein, a novel indolyl substituted metal-allyl zwitterionic intermediates through the decarboxylation of conveniently available vinyl indoloxazolidones, which could be regarded as two types of dipolar species through the anionic delocalization was disclosed. The palladium-π-allyl species tended to served as an all-carbon 1,3-dipole in the asym. [3+2] cycloaddition with electron-deficient alkenes, which furnished polysubstituted cyclopenta[b]indoles I [R1 = H, 7-F, 7-Cl, etc.; R2 = Ph, 1-naphthyl, 2-furanyl, etc.; R3 = CN, CO2Me] with high regio- and stereoselectivities. Meanwhile, the iridium-π-allyl species was recognized as an aza-1,3-dipole in asym. [3+2] cycloaddition with in situ generated C1 ammonium enolates, afforded pyrrolo[1,2-a]indoles II [R1 = H, 7-F, 7-Cl, etc.; R4 = CH:CHCH3, Ph, 3-thienyl, etc.] with high diastereo- and enantioselectivities. In addition, the dipolar cycloadditions could be easily scaled-up and several synthetic transformations of the cycloadducts were demonstrated for the rapid synthesis of diverse chiral polycyclic indoles.
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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem