is methyl anthranilate a heteroatom or hydrocarbon?
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is methyl anthranilate a heteroatom or hydrocarbon?
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Explanation:
Six-membered Rings with Three or more Heteroatoms, and their Fused Carbocyclic Derivatives
P.M. Weintraub, in Comprehensive Heterocyclic Chemistry III, 2008
9.07.11.3 2,1,3-Benzothiadiazines
Cyclization of methyl anthranilates with sulfamyl chloride affords 2,1,3-benzothiadiazin-4-ones (Section 9.07.9.1.1). The less common 1H-2,1,3-benzothiadiazine 2,2-dioxides were obtained in modest yield by reaction of 2-hydroxymethyl anilines with Burgess reagent (Section 9.07.9.1.1). A two-step process starting from ortho-iodosulfamides, via generation of a trianion, condensation with an aldehyde, and subsequent acid-catalyzed cyclization, led efficiently to 4-substituted-3,4-dihydro-1H-2,1,3-benzothiazine 2,2-dioxides (Section 9.07.9.2.2).
Condensation of ortho-amino acetophenones with sulfamide affords 4-substituted-1H-2,1,3-benzothiadizine 2,2-dioxides (Section 9.07.9.1.3). An interesting approach to the same class of compounds involves Grignard addition to anthranilonitrile followed by addition of sulfuryl chloride (Section 9.07.9.2.1). The 1H-1,2,6-benzothiadiazine 2,2-dioxide ring was constructed by treatment of an ortho-aminomethyl aniline with sulfamide in pyridine at reflux (Section 9.07.9.2.2).
Pyrazino[2.3-c][1,2,6]thiadiazine 2,2-dioxides were prepared by condensation of 4,5,6-triamino-1,2,6-thiadiazine 1,1-dioxide with 1,2-diketones. Regioselectivity was achieved as the more reactive carbonyl reacted with the 4-amino group. Alternately, selectivity could be attained by use of α-oximino ketones (Section 9.07.7.2).
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