1,4-Disubstituted and 1,4,5-Trisubstituted 2-[(Benzotriazol-1-yl)methyl]pyrroles as Versatile Synthetic Intermediates
- 1 January 1996
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 61 (5) , 1624-1628
- https://doi.org/10.1021/jo951894m
Abstract
The CH2Bt substituent, unlike previously used CH2X substituents, enables (i) the synthetic elaboration of pyrroles with unsubstituted ring positions and (ii) electrophilic as well as nucleophilic substitutions to give pyrroles of type pyrrolyl-2-CHENu. Thus, 1,4-disubstituted (7) and 1,4,5-trisubstituted 2-[(benzotriazol-1-yl)methyl]pyrroles (15) were easily prepared from the reaction of 5-(benzotriazol-1-yl)-1,2-epoxy-3-pentynes 4 or 14 with primary amines in i-PrOH. The 2-(benzotriazol-1-yl)methyl side chains of compounds 7 and 15 were elaborated by nucleophilic substitution and also by initial alkylation followed by replacement or elimination of the benzotriazolyl moiety to afford a variety of 1,2,4-trisubstituted (6, 8−9, 11−13) and 1,2,4,5-tetrasubstituted pyrroles (18, 20−22).Keywords
This publication has 17 references indexed in Scilit:
- The Origins of the Benzotriazole Project, Its Versatility Illustrated by a New -C=CHCH+OEt Synthon, and Novel Syntheses of α,β-Unsaturated Aldehydes and Ketones, Furans, Pyrroles and Allyl EthersSynthesis, 1995
- A Novel Furan Ring Construction and Syntheses of 4- and 4,5-Substituted 2-(.alpha.-Heterocyclylalkyl)furansThe Journal of Organic Chemistry, 1995
- Thermal Rearrangement of N-Alkyl-, and N-Aryl-(2,2-dihalo-1-phenylcyclopropyl)methyleneamines to 1-Alkyl-, and 1-Aryl-2 (or 3)-halo-4-phenylpyrrolesBulletin of the Chemical Society of Japan, 1995
- Synthesis of 2-(Substituted Methyl)-3,4-Disubstituted Pyrroles and Their Conversion into the Corresponding PorphyrinsBulletin of the Chemical Society of Japan, 1992
- N-Vinyl-,N-Allyl-,N-Propenyl- andN-Propargyl-benzotriazoles: Reactions of Their Lithium DerivativesEuropean Journal of Organic Chemistry, 1992
- An Improved Method for the Preparation of Symmetrically Substituted Porphyrins via 2-Methoxymethyl-3,4-disubstituted Pyrrole DerivativesChemistry Letters, 1989
- Die Struktur des blauen Pyrrolfarbstoffs aus 5-Brom-2,4-dimethyl-3-pyrrolcarbonsäure-ethylesterEuropean Journal of Organic Chemistry, 1978
- "Abnormal" displacement in the reaction of 2-(N-methylpyrrolyl)methyltrimethylammonium salts with sodium cyanideThe Journal of Organic Chemistry, 1977
- Synthesis of 2-aminomethyldipyrrolylmethanes of biosynthetic interestJournal of the American Chemical Society, 1971
- Recent Advances in the Chemistry of Pyrrole.Chemical Reviews, 1963