Derivatives of 4-(Aminomethyl)pyrrole-3-carboxylic Acid

Arnold, D. P.; Brown, Rfc; Nitschinsk, LJ; Perlmutter, Patrick; Tope, HK

doi:10.1071/ch9940975

Cited by 6 publications

(2 citation statements)

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“…The tosyl imidazoles 57 synthesized using this method are listed in Table VII [39]. No reaction was observed when R was the tert-butyl group in the imidoyl chlorides [40] since the product hydrolyzes into the corresponding amide before reaction takes place.…”

Section: Imidazolesmentioning

confidence: 98%

“…The yield was improved to 87% by using 2.4 equivalents of t-BuOK at À80 C in THF in the reaction between TosMIC and the extended Michael acceptor 147 as outlined in Scheme 55. The variation in Michael acceptor 120 where R represents a second electronwithdrawing group is feasible with two different electron-withdrawing groups in 120; the reaction with TosMIC affords a single pyrrole 155 [58] (Scheme 59). The Michael acceptor activity can be further increased by using two electronwithdrawing groups at the same carbon atom (160) to form a pyrrole 161; one of these groups has to be removed during the course of reaction with TosMIC (Scheme 62) [61].…”

Section: Imidazolesmentioning

confidence: 99%

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p -Toluenesulfonylmethyl Isocyanide: a Versatile Synthon in Organic Chemistry

Tandon¹,

Rajagopalan²

2003

Sulfur Reports

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TosMIC, a versatile synthon in organic chemistry, has been extensively used for the synthesis of a wide variety of small, medium and large ring heterocycles. It has immense implications in the synthesis of nitriles, aldehydes, ketones, alkanes, cyclophanes and large number of natural products. Several drug intermediates and pharmacologically active compounds have been synthesized from TosMIC. In addition, chiral TosMIC analogs have been synthesized and employed for synthesis of optically active compounds.

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Section: Imidazolesmentioning

confidence: 98%

Section: Imidazolesmentioning

confidence: 99%

p -Toluenesulfonylmethyl Isocyanide: a Versatile Synthon in Organic Chemistry

Tandon¹,

Rajagopalan²

2003

Sulfur Reports

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Synthetic Uses of Tosylmethyl Isocyanide (TosMIC)

Leusen

2001

Organic Reactions

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TosMIC is the acronym for 4‐tolylsulfonylmethyl isocyanide or tosylmethyl isocyanide. It is the best‐known member of a series of about 25 sulfonyl‐substituted methyl isocyanides RSO 2 CH 2 NC collected in Chart 1 (p. 426). TosMIC is a multipurpose synthetic reagent. It is by far the most versatile synthon derived from methyl isocyanide. This chapter provides a complete account of the synthetic uses of TosMIC based on a literature search closed in January 1996, and supplemented with further data available to the authors. Also included are applications of some of the more important TosMIC homologs (TosCHRNC). TosMIC is the only commercially available sulfonylmethyl isocyanide. It is a stable, colorless, practically odorless solid, which can be stored at room temperature without decomposition. Four brief review papers on the chemistry of TosMIC have appeared, in 1980, 1987, 1993, and 1995. Several reviews on the chemistry of isocyanides in general are available. An effort has been made to make this chapter as complete as possible, in coverage both by tables and by references, with respect to the immediate objective: a survey of the “Synthetic Uses of TosMIC.” Emphasis is on the primary products derived from reactions of TosMIC and related isocyanides, with limited reference to the further utilization of these products. Thus, the next section gives a complete account of reductive cyanation, the conversion of aldehydes or ketones into cyanides with the use of TosMIC, but for obvious reasons synthetic applications of the product cyanides are not treated in this chapter. One of the subsequent sections describes the application of TosMIC to the synthesis of pyrroles, including 2,3‐divinylpyrroles, which are important precursors in a new synthesis of indoles. This latter transformation, made possible by the easy availability of the precursors through TosMIC chemistry, is afforded brief coverage. As a rule, reference to preliminary papers has been omitted when the same information is available from the corresponding full papers. The patent literature is covered highly selectively and is cited only when providing new and relevant information. Negative results of reactions are reported in the text or tables only when at least some relevant information is available with respect to the conditions of such unsuccessful attempts.

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