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Indole is used in the preparation of gramine, which is obtained by Mannich reaction dimethylamine and formaldehyde. It is used as a starting material for the preparation of oxindole and indole-3-carboxaldehyde. In Diels-Alder reaction, it acts as dienophile and reacts with 2-aminofuran to get strychnine. It is the active component of jasmine oil, neroli oil and orange-blossom oil used in the perfume industry. Further, it is involved in the preparation of synthetic jasmine oil.
Lithiation of N-protected indoles usually occurs at the 2-position, e.g. benzenesulfonation of the 1-lithio derivative, 2-lithiation with LDA and treatment with pyridine-3,4-dicarboxylic anhydride. This sequence has been reported in a synthetic route to ellipticene and olivacine: J. Org. Chem., 57, 5891 (1992).
Regioselective synthesis of 3-substituted indoles has been described using a sequence of N-silylation, 3-bromination of the 1-TBDMS detivative with NBS, 3-lithiation, treatment with an electrophile to introduce the 3-substituent, and desilylation with TBAF. Good overall yields are obtained for a range of electrophiles: J. Org. Chem., 59, 10 (1994); Org. Synth. Coll., 9, 417 (1998).
Treatment with EtMgI followed by ZnCl2 leads to an N-zinc derivative. This undergoes acylation at the 3-position: Tetrahedron, 46, 6061 (1990).
Halogenation in the 2-position has been effected via the Li 1-carbamate and subsequent 2-lithiation: J. Org. Chem., 57, 2495 (1992):
Treatment of the carbamate with Tri-n-butyltin chloride, A10746, followed by Stille coupling enables synthesis of 2-aryl- and 2-vinylindoles: J. Org. Chem., 60, 6218 (1995).
Johnston, A. J.; Zhang, Y. R.; Busch, S.; Pardo, L. C.; Imberti, S.; McLain, S. E. Amphipathic Solvation of Indole: Implications for the Role of Tryptophan in Membrane Proteins. J. Phys. Chem. B 2015, 119 (19), 5979-5987.
Yang, P.; Pang, M.; Shen, W.; Li, M.; He, R. Vibronic analysis of the 1Lb ? S0 transitions of indole and 3-methylindole: The influence of anharmonic, Duschinsky, and Herzberg-Teller contributions. J. Mol. Spectrosc. 2015, 313, 40-48.
Hazard Statements: H302-H311-H317-H318
Harmful if swallowed. Toxic in contact with skin. May cause an allergic skin reaction. Causes serious eye damage.
Precautionary Statements: P261-P264b-P270-P272-P280-P301+P312-P302+P352-P305+P351+P338-P310-P312-P330-P333+P313-P361-P363-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Contaminated work clothing should not be allowed out of the workplace. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN: Wash with plenty of soap and water. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. If skin irritation or rash occurs: Get medical advice/attention. Remove/Take off immediately all contaminated clothing. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant